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The endemic New Zealand lichenPannaria xanthomelanahas been restudied and found to be characterized by a secondary chemistry of pannarin and porphyrilic acid in addition to terpenoids, and by always having abundant, conspicuously large, and mostly foliose cephalodia. Its verruciform pycnidia and bacilliform pycnoconidia/spermatia are described here for the first time. Two other related New Zealand endemics,P. gallowayiandP. aotearoana, are described as new. Both have small, relatively rare and inconspicuous cephalodia. They contain a new chemosyndrome, with pannarin, contortin andO-methyl-leprolomin together with major quantities of several unidentified terpenoids, previously reported from the related Australian species,P. isidiata.O-methyl-leprolomin is a novel compound, with similar TLC properties to leprolomin, but with different Rfvalues. Most collections of both species from the North and the South Islands of New Zealand contain additional porphyrilic acid. However, this compound is absent from many collections of these species from the subantarctic Campbell and Auckland Islands. Aside from chemistry,Pannaria gallowayiis also distinguished by having broad, papery lobes.Pannaria aotearoanawhich appears to be the more common species, has a thick thallus and characteristic thick, convex, marginal phyllidia, larger spermatia and more conspicuous pycnidia thanP. gallowayiandP. xanthomelana. The three species share two different major chlorobionts.Trebouxiadominates in the north, and is gradually replaced southwards by a type provisionally called cf.Myrmecia.

The lichen-forming fungal genus Flavoparmeliaincludes species with distinct distribution patterns, including subcosmopolitan, restricted, and disjunct species. We used a dataset of nuclear ITS and LSU ribosomal DNA including 51 specimens to understand the influence of historical events on the current distribution patterns in the genus. We employed Bayesian, maximum likelihood and maximum parsimony approaches for phylogenetic analyses, a likelihood-based approach to ancestral area reconstruction, and a Bayesian approach to estimate divergence times of major lineages within the genus. We identified two major clades in the genus, one of them separating into two subclades and one of those into four groups. Several of the groups and clades have restricted geographical ranges in the Southern Hemisphere, but two groups include species with wider distribution areas. Our analyses suggest that the genus originated in southern South America during the Eocene–Oligocene transition and that the diversification of the Australasian groups occurred recently. The subcosmopolitan distribution of species is explained by long-distance dispersal, while vicariance probably played a major role in the origin of the genus. Several currently accepted species were found to be non-monophyletic, indicating that the species delimitation in the genus requires further studies.

The new species Zwackhiomyces sulcatus sp. nov. growing on Austroparmelina macrospora from Australia is described as new to science. This species represents the first lichenicolous fungus found growing on this recently described Southern Hemisphere parmelioid genus. The most important characters are discussed and compared to morphologically closely related species.

The new species, Cresponea sorediataElix, Øvstedal & Gremmen, based on material from Gough Island, is described. It is characterized by a sorediate thallus, but no apothecia has been found. The diagnostic substances of the new species are usnic acid, isousnic acid and consimonyellin.

Lecanora peninsularisfrom the San Jacinto Mountains of southern California in western North America is described as new to science. The species is lignicolous and apparently related to L. crassithallina, presently known only from Mexico. The main diagnostic substances present in the new species are isousnic acid, gyrophoric acid, and 7-O-methylnorascomatic acid.

Parmelioid lichens are a diverse and ubiquitous group of foliose lichens. Generic delimitation in parmelioid lichens has been in a state of flux since the late 1960s with the segregation of the large, heterogeneous genus Parmelia into numerous smaller genera. Recent molecular phylogenetic studies have demonstrated that some of these new genera were monophyletic, some were not, and others, previously believed to be unrelated, fell within single monophyletic groups, indicating the need for a revision of the generic delimitations. This study aims to give an overview of current knowledge of the major clades of all parmelioid lichens. For this, we assembled a dataset of 762 specimens, including 31 of 33 currently accepted parmelioid genera (and 63 of 84 accepted genera of Parmeliaceae). We performed maximum likelihood and Bayesian analyses of combined datasets including two, three and four loci. Based on these phylogenies and the correlation of morphological and chemical characters that characterize monophyletic groups, we accept 27 genera within nine main clades. We re-circumscribe several genera and reduce Parmelaria to synonymy with Parmotrema. Emodomelanelia Divakar & A. Crespo is described as a new genus (type: E. masonii). Nipponoparmelia (Kurok.) K.H. Moon, Y. Ohmura & Kashiw. ex A. Crespo & al. is elevated to generic rank and 15 new combinations are proposed (in the genera Flavoparmelia, Parmotrema, Myelochroa, Melanelixia and Nipponoparmelia). A short discussion of the accepted genera is provided and remaining challenges and areas requiring additional taxon sampling are identified.

Phylogenetic relationships of the genera Cladiaand Heterodeawere reconstructed using a combined dataset of nuclear ITS, nuclear LSU and mitochondrial SSU rDNA sequences. Based on different analyses (Bayesian approach, maximum parsimony, maximum likelihood), the ingroup (Cladia+ Heterodea) is strongly supported as monophyletic. Pilophorus strumaticushas a well supported sister–group relationship to the ingroup and together they form a sister group with a well–supported clade, which includes Metus conglomeratusand Pycnothelia papillaria. The Shimodaira–Hasegawa test and the ELW test significantly rejected monophyly of Cladiaexcluding Heterodea. Within Cladiathree main clades can be distinguished which share morphological and chemical characters. The position of the foliose genus Heterodeawithin the fruticose Cladiais supported by anatomical and chemical characters. The species of clade II that includes two Cladiaspecies and Heterodeashare a similar type of upper cortex and two–layered medulla with an inner or lower medulla consisting of dark pigmented, thick–walled hyphae. Our phylogenetic estimate and the anatomical studies indicate that the foliose thallus of Heterodeaoriginated from pseudopodetia of Cladia. It is discussed that the species currently classified in Cladiaand Heterodeaneed to be placed in the same genus.

Species delimitation in lichens of the Physcia aipolia group in Australia has been studied based on thalline morphology (lobe width, upper surface pruinosity) and medullary triterpene chemistry as main character complexes. Previous treatments have utilised the presence or absence of atranorin and zeorin in the medulla as useful discriminators, but have neglected utilising the diversity of medullary triterpenes for taxonomic purposes. We have now tested the phylogenetic patterns of distribution of subtle morphological characters and terpenoid chemistry by means of molecular phylogenetic analysis of nuclear ITS and mitochondrial SSU rDNA sequences. Our analysis supports triterpene chemosyndromes and subtle morphological characters for the distinction of distinct lineages. Three new species are described for Australia, P. austrostellaris Elix, P. littoralis Elix and P. tropica Elix. In addition, the detailed chemical variation of species within the group is documented and three major chemosyndromes of triterpenes have been identified.

The new species,Brigantiaea leprosaKantvilas & Elix, based on material from Tasmania and New South Wales, is described. It is characterised chiefly by a leprose-sorediate thallus, with the soredia arising from scattered pustules, and by the presence of caloploicin and vicanicin in addition to atranorin and zeorin.

Pertusaria labuensisA. W. Archer & Elix andP. mankiensis A. W. Archer & Elix, from Papua New Guinea,P. palumensisElix & A. W. Archer andP.wallamanensis Elix & A. W. Archer, from Australia,P. simoneanaA. W. Archer & Elix from New Caledonia andP. wilsonii, A. W. Archer & Elix from Vanuatu are reported as new to science. Pertusaria balekensisA. W. Archer & Elix,P. buburanaElix & A. W. Archer andP. oblongata Müll. Arg. are reported as new records for Australia,Pertusaria hypochryseaVain. for New Caledonia andP. pilosulavar.abditivaJariangprasert andP. roseolaA. W. Archer & Elix for Papua New Guinea.Pertusaria howeana A. W. Archer & Elix is reported as a later synonym ofP. oblongataMüll. Arg.

It has been suggested that the usnic acid-containing species of Lepraria do not belong to Lepraria s. str. In addition, the two usnic acid-containing Lepraria species, Lepraria usnica Sipman and Lepraria coriensis (Hue) Sipman, were suspected to be conspecific by some authors. We incorporate molecular sequence data from two independent loci to test several hypotheses regarding the conspecificity and phylogenetic position of these two taxa. The two species do not form a monophyletic clade, thereby rejecting conspecificity, but both fall outside Lepraria s. str. The placement of L. usnica in Pilocarpaceae is well supported, while the familial placement of L. coriensis could not be determined; the species clusters with taxa outside Lecanorales s. str. This study further illustrates the polyphyly of the leprose growth form and also suggests that certain leprarioid lichens may represent sterile forms of otherwise well-known genera, such as Sporopodium in the Pilocarpaceae.

The secondary metabolites of eleven species belonging to the Neuropogon group in Usnea have been investigated using thin-layer and high performance liquid chromatography. In addition to usnic acid, eight chemosyndromes were found including the echinocarpic acid and neotricone chemosyndromes, which are reported for Usnea for the first time. Seventeen compounds are reported for the first time for the Neuropogon group. The new substances isomyelochroic acid and protoneuropogolic acid are described.

Parmotremais one of the larger genera segregated from Parmelia s. lat.Additional genera recently have been segregated from this large genus based mainly on morphological and chemical features. We have employed molecular data from three genes to continue a revision of the generic concept within the parmelioid lichens. A Bayesian analysis of nuclear ITS, LSU rDNA and mitochondrial SSU rDNA sequences was performed. The genera Canomaculina, Concamerella, Parmelariaand Rimeliaappear nested within Parmotrema.Alternative hypotheses to maintain the independence of Canomaculina, Concamerellaand Rimeliaare shown to be highly unlikely and are rejected. As a consequence these three genera are reduced to synonymy with Parmotrema.An alternative topology segregating Parmelariafrom Parmotrema s. lat.cannot be rejected with the dataset at hand. However we have established that this genus is closely related to Parmotremarather than to cetrarioid species as was considered previously. The revised genus Parmotremaincludes species that have an upper cortex consisting of a palisade plectenchyma or rarely paraplectenchyma with vaults, have a pored or fenestrated epicortex, lack pseudocyphellae, have or lack cilia, have laminal, perforate or eperforate apothecia, usually have simple rhizines and filiform, cylindrical, bacilliform or sublageniform conidia. It is closely related to Flavoparmeliabut the status of these genera requires further investigation. Nineteen new combinations are made.

Generic concepts in the parmelioid lichens have been discussed intensively over the past three decades without reaching a broad consensus. We have now employed molecular data from three genes to provide a basis for a revised generic concept of the parmelioid lichens containing Xanthoparmelia­type lichenan. The phylogeny of the parmelioid lichens containing Xanthoparmelia­type lichenan was reconstructed using a combined Bayesian analysis of nuclear ITS, LSU rDNA and mitochondrial SSU rDNA sequences, and a maximum parsimony analysis was also made for comparison. 179 new partial sequences of 58 taxa were generated and 12 sequences were downloaded from GenBank. Our results indicate that the lichens containing Xanthoparmelia­type lichenan form a monophyletic group. However, the segregates proposed earlier do not form distinct clades within the group. Alternative hypotheses of monophyletic Karoowiaand Neofusceliathat are not nested within Xanthoparmeliawere rejected with our dataset; Karoowiais polyphyletic, and Neofusceliais reduced to synonymy under Xanthoparmelia. Xanthomaculina convolutaalso belongs to Xanthoparmelia. Since we were unable to sequence the umbilicate type species of Xanthomaculina, we refrain from synonymizing that genus with Xanthoparmeliahere. The synonymy of Chondropsisand Paraparmeliaunder Xanthoparmeliaalready proposed is supported. The revised and enlarged genus Xanthoparmeliaincludes species that have cell walls with Xanthoparmelia­type lichenan, a palisade plectenchyma with a pored epicortex, lack pseudocyphellae, with usually simple rhizines, generally bifusiform conidia, and medullary chemical diversity. Ten new names are proposed, and 129 new combinations are made into Xanthoparmelia.

Abstract:

Abstract:

Die Struktur von zwei neuen Anthrachinonen, 7-Chloroemodinal (6) und 7-Chloroemodsäure (7), die in der Flechte Caloplaca spitsbergensis auftreten, wird mit spektroskopischen Studien aufgeklärt. Die neuen Anthrachinone kommen mit den bekannten Anthrachinonabkömmlingen Parietin (2), Emodin (1), 7-Chloremodin (3), 7-Chlorcitreorosein (5), 1-O-Methyl-7-chloremodin (4) und 7- Chlor-1,6,8-trihidroxy-3-methyl-10-anthron (8) vor.

Abstract:The morphology, anatomy, chemistry and ecology of some corticolous and lignicolous species of Buelliafrom the lberian Peninsula that contain secondary lichen compounds are discussed, including B. chloroleuca, B. disciformis, B. erubescens, B. hyperbolicaand B. leptoclinoides. These species are compared with other corticolous Buelliaspecies that occur outside the study area, including B. arnoldii, B. insignis, B. regularisand B. sanguinolenta. The misunderstood B. zahlbruckneriJ. Steiner and B. jorgei, are synonyms of B. erubescens, and the invalid taxon B. zahlbrucknerisensu Schauer non Steiner and B. poeltii, are synonyms of B. chloroleuca. New chemical data on several taxa are reported. A key to the species and illustrations of their ascospores are provided.

A new pyranonaphthazarin, coronatoquinone [(1S)-1,5,8,10-tetrahydroxy-7-methoxy-3-methyl-6,9-dihydro-1H-naphtho[2,3-c]pyran-6,9-dione] (1), has been isolated from the lichen Pseudocyphellaria coronata. The structure of coronatoquinone (1) was established by spectroscopic methods and its absolute configuration determined from chiroptical measurements. Keywords. Isolation; lichen; natural product; quinone.

Three new β-orcinol depsidones belonging to the stictic acid chemosyndrome, namely peristictic acid (1,4-dihydroxy-10-methoxy-5,8-dimethyl-3,7-dioxo-1,3-dihydro-7H-isobenzofuro[4,5-b][1,4]benzodioxepin-11-carboxylic acid) (9), lusitanic acid (methyl 1,4-dihydroxy-10-methoxy-5,8-dimethyl-3,7-dioxo-1,3-dihydro-7H-isobenzofuro[4,5-b][1,4]benzodioxepin-11-carboxylate) (10) and verrucigeric acid (1,4-dihydroxy-11-hydroxymethyl-10-methoxy-5,8-dimethyl-3,7-dioxo-1,3-dihydro-7H-isobenzofuro[4,5-b][1,4]benzodioxepin-1,11-diyl hydrogen orthoacetate) (14) have been identified in the lichens Relicina sydneyensis and Xanthoparmelia verrucigera respectively. The structure of the new depsidones followed from a combination of partial syntheses, chromatographic comparisons and spectroscopic data. Keywords. Depsidone; stictic acid; chemosyndrome; lichen; chromatography; mass spectrometry; n.m.r.

Ten parmelioid taxa in five genera were identified from Rarotonga, Cook Islands, South Pacific Ocean. These comprise: three species of Bulbothrix, one species of Canoparmelia, four species of Parmotrema, one species of Rimeliaand one species of Xanthoparmelia. Canoparmelia rarotongensisLouwhoff & Elix is described as new, being distinguished from other species of this genus by its unique secondary chemistry (lecanoric acid) and conspicuous, inflated isidia. The majority of parmelioid lichens on Rarotonga have cosmopolitan and pantropical distributions.Bulbothrixis reported for the first time from the Polynesian region.

The scabrosin esters (1){(4), isolated from the lichen Xanthoparmelia scabrosa, were reanalysed by modern one- and two-dimensional n.m.r. spectroscopic methods, including 15N n.m.r. spectroscopy, and single-crystal X-ray structural analysis. This reinvestigation has resulted in the unambiguous structure elucidation and complete spectral assignment of these metabolites and established them to be a family of epidithiopiperazinedione derivatives. A new scabrosin ester, scabrosin butyrate hexanoate (5), has also been isolated and its structure determined, including assignment of absolute configuration. Several scabrosins were found to exhibit potent cytotoxic activity against the murine P815 mastocytomia cell line (IC50c. 0·5 µM) and the human breast MCF7 carcinoma cell line (IC50c. nM). Compounds which contain a dithiopiperazinedione moiety have not previously been identified in lichenized fungi.

The new depsides decarboxyhypothamnolic acid [3-(2′,4′-dihydroxy-3′,6′-dimethylphenyloxycarbonyl)-2- hydroxy-6-methoxy-4-methylbenzoic acid] (4) and cryptothamnolic acid [3-(3′-formyl-2′-hydroxy-4′-methoxy- 6′-methylbenzoyloxy)-4,6-dihydroxy-2,5-dimethylbenzoic acid] (6) have been detected in extracts of a Chinese Pertusariaspecies together with hypothamnolic acid (3) and their structures implied by means of chromatographic and spectroscopic comparisons with synthetic materials. Two further new depsides, neothamnolic acid [3-(5′,7′- dihydroxy-6′ -methyl-1′ -oxo-1′ ,3′ -dihydroisobenzofuran-4′ -yloxycarbonyl)-2-hydroxy-6-methoxy-4- methylbenzoic acid] (8) and lactothamnolic acid [3-(6′-formyl-5′,7′-dihydroxy-1′-oxo-1′,3′-dihydroisobenzo- furan-4′-yloxycarbonyl)-2-hydroxy-6-methoxy-4-methylbenzoic acid] (9), have been isolated from the lichen Siphula ramalinoides, and the structure of these compounds followed from a combination of spectroscopic data, derivatization and degradation experiments.

The depsidones chalybaeizanic acid (1,4,10-trihydroxy-8-methyl-3,7-dioxo-1,3-dihydro-7 H-isobenzofuro- [4,5-b][1,4]benzodioxepin-5,11-dicarbaldehyde) (4) and quaesitic acid (11-formyl-1,4,10-trihydroxy-8- methyl-3,7-dioxo-1,3-dihydro-7 H-isobenzofuro[4,5-b][1,4]benzodioxepin-5-methyl hydrogen fumarate) (5) have been isolated from the lichens Xanthoparmelia amphixanthoidesand Hypotrachyna quaesitarespectively, and their structures determined by a combination of spectroscopic evidence, partial synthesis, derivatization or degradation reactions.

Abstract:Morphological and chemical data from 64 genera of Parmeliaceae, including the most common genera in Europe, were analysed by means of neighbour-joining and parsimony analysis. Two presence/absence matrices were constructed, one for the 64 genera and a smaller one for the most common European genera. Probabilities were too low to allow grouping of the genera and only a few pairs of genera had a probability of >50% for both matrices. A molecular matrix (nuclear rDNA-ITS) of the most common genera in Europe was constructed and analysed by the method of maximum likelihood. These results were much more informative than the non-molecular matrix for establishing phylogenetic relationships among the genera.

Hybocarpone ( 1), a novel pentacyclic naphthazarin-derived dimer has been isolated from mycobiont cultures derived from the lichen Lecanora hybocarpa. The structure of hybocarpone ( 1) was established on the basis of 1D and 2D NMR spectroscopy. Its relative stereochemistry was predicted with the use of molecular modelling and confirmed by X-ray crystallographic analysis. Hybocarpone ( 1) was found to be a potent cytotoxin (IC 50c0.27 μM), active against the murine P815 mastocytoma cell line.

The new crustose lichen genus Tasmidella, containing the species, T. variabilissp. nov. with two varieties, var. variabilisand var. inactivavar. nov., is described. Tasmidellais most closely related to Megalaria, from which it differs chiefly by having simple ascospores with a layered wall. Relationships with superficially similar genera are discussed. A revised circumscription of the family Megalariaceaeis provided to take into account the inclusion of a second genus.

Total syntheses of the p-terphenyls butlerin A (1) (3′,4,4′′,6′-tetramethoxy[1,1′:4′,1′′-terphenyl]-2′-yl acetate), butlerin B (2) (3′,4,4′′,5′-tetramethoxy[1,1′:4′,1′′-terphenyl]-2′-yl acetate) and butlerin C (3) (3′,4,4′′-trimethoxy[1,1′:4′,1′′-terphenyl]-2′,6′-diyl diacetate), previously isolated from the lichen Relicina connivens, are reported.

The unambiguous total synthesis of ten O-methyl and/or C-hydroxy derivatives of gyrophoric acid (1) has been achieved by using the condensation of an appropriately substituted benzoic acid and benzyl lecanorate (33) or benzyl 2-O-methyllecanorate (32) in the key step.

Three species which contain both gyrophoric and lecanoric acids and possess perithecioid ascomata are recognized in the genusDiploschistes. D. badius andD. gyrophoricus are described as new, whileD. subcupreus is reduced to synonymy withD. sticticus. Two species occur in the southern hemisphere, whileD. badius is found in N. America.

The diphenyl ether epiphorellic acid 3 [6-hydroxy-3-(5′-hydroxy-2′-methoxycarbonyl-3′-propylphenoxy)-4-methoxy-2-pentylbenzoic acid] (3) has been prepared by unambiguous synthesis, and has been detected in the lichen Coelopogon abraxasby chromatographic and spectroscopic comparisons.

The new depsides 3,5-dichloro-2′-O-methylnorstenosporic acid (4), 5-chloro-2′-O-methylanziaic acid (5) and 3,5-dichloro-2′-O-methylnorhyperlatolic acid (6) have been detected in the lichenLecanora lividocinereaand the structures of these metabolites have been established by unambiguous synthesis. In addition, the synthesis of the depside 3,5-dichloro-4-O-demethylplanaic acid (7) is described.

Numerous samples of Anamylopsora pulcherrima and Tephromela armeniaca have been chemically investigated. A. pulcherrima contains alectorialic acid, alectorialin, and 5,7-dihydroxy-6-methylphthalide, and T. armeniaca the same compounds and additionally roccellic acid and barbatolic acid.

The structure of two new dibenzofuran derivatives present in the lichen genus Haematomma has been established by synthetic and ¹H n.m.r. spectroscopic studies. Isopseudoplacodiolic acid (= usnic acid isomethoxide) (9) and isoplacodiolic acid (10) have been shown to co-occur together with atranorin in Haematomma flexuosum Hillmann and H. matogrossense Kalb & Staiger.

The depsidones sublobaric acid (8-hydroxy-3-methoxy-11-oxo-1-propanoyl-6-pentyl-11H-dibenzo[b,e][1,4]- dioxepin-7-carboxylic acid) (6) and oxolobaric acid (1-(1′,4′-dioxopentyl)-8-hydroxy-3-methoxy-11-oxo-6-pentyl-11H-dibenzo[b,e][1,4]dioxepin-7-carboxylic acid) (7) have been isolated from the lichenAnzia hypoleucoidestogether with atranorin, chloroatranorin, divaricatic acid and lobaric acid (1). The structure of compounds (6) and (7) followed from a combination of spectroscopic data.

The unambiguous total synthesis of the lichen depsides 2-O-methylglomelliferic acid (39), 4-O- methylhyperolivetoric acid (40), hyperconfluentic acid (41), microphyllinic acid (42), arthoniaic acid (43), 2′-O-methylmicrophyllinic acid (44), 2′-O-methylhyperphyllinic acid B (45), 4-O-methylsuperolivetoric acid (46), 2′-O-methylhyperphyllinic acid A (47), 2′-O-methylnorsuperphyllinic acid (48) and 4-O- methyloxocryptochlorophaeic acid (49) has been achieved by the condensation of an appropriately substituted orsellinic acid and protected phenol in the key step, followed by deprotection.

The structure of the unique monoterpene glycoside, lactiflorin, a constituent of several species of Paeoniawith medicinal properties, has been determined by spectroscopic techniques.

The new depsides decarboxydivaricatic acid (3), decarboxy-2′-O-methyldivaricatic acid (4), de- carboxynorstenosporic acid (5), decarboxynorimbricaric acid (6), decarboxystenosporic acid (7), decarboxy-2′-O-methylnorimbricaric acid (8), decarboxyanziaic acid (9) and decarboxyperlatolic acid (10), and the novel tridepsides depsidellin A (23), depsidellin B (27) and depsidellin C (29) have been detected in the lichen Neofuscelia depsidellaand their structures determined by total synthesis

Two new -orcinol depsidones, 1and 2, together with 13 known compounds were isolated from the lichen Usnea articulata. The structures of 1and 2were elucidated by spectroscopic analyses and those of known compounds by comparison of their spectroscopic data with literature values or by direct comparison with authentic standards. Compounds 1, 2, and 5exhibited moderate antiradical activity in the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. The depsidones 4and 5showed better superoxide anion scavenging activity (IC50566 and 580 M, respectively) than quercetin (IC50754 M).

The new naphthopyrone, pigmentosin A 1, has been isolated from the lichen Hypotrachyna immaculata and its structure elucidated using multidimensional NMR spectroscopic methods, including high-field (600 MHz) gHMBC and gHMQC experiments. This compound is the first lichen metabolite known to contain a bisnaphthopyrone moiety in its structure.

A concise and versatile route to functionalised naphthazarins via 1,3,4,5,6,8-hexamethoxynaphthalene is described and is illustrated with the synthesis of three natural products, aureoquinone, boryquinone and 3-ethyl-2,7-dihydroxynaphthazarin.