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This minireview showcases the role indole diterpenoids have played in inspiring the development of clever synthetic strategies and new chemical reactions., Indole terpenoids comprise a large class of natural products with diverse structural topologies and a broad range of biological activities. Accordingly, indole terpenoids have and continue to serve as attractive targets for chemical synthesis. Many synthetic efforts over the past few years have focused on a subclass of this family, the indole diterpenoids. This minireview showcases the role indole diterpenoids have played in inspiring the recent development of clever synthetic strategies, and new chemical reactions.

Several novel benzoxaborole derivatives were synthesized starting from 2-formylphenylboronic acid utilizing Baylis–Hillman reaction, Barbier allylation, Passerini reaction, and aldol reaction protocols as the key step. All the synthesized benzoxaboroles have been evaluated for their antibacterial, antifungal, and anticancer activities.

Dimeric indole alkaloids are structurally diverse natural products that have attracted significant attention from the synthetic and biosynthetic communities. Here we describe the characterization of a P450 monooxygenase CnsC from Penicillium that catalyzes the heterodimeric coupling between two different indole moieties, tryptamine and aurantioclavine, to construct vicinal quaternary stereocenters and yield the heptacyclic communesin scaffold. We show, using biochemical characterization, substrate analogs, and computational methods, that CnsC not only catalyzes the C3-C3 carbon-carbon bond formation, but also controls the regioselectivities of the pair of subsequent aminal bond formations to yield the communesin core. The use of ω-N-methyltryptamine and tryptophol in place to tryptamine led to the enzymatic synthesis of isocommunesin compounds, which have not been isolated to date.

Covering: up to 2014 In the developing world, multi-drug resistant malaria caused by the parasite Plasmodium falciparum is an epidemic that claims the lives of 1–3 million people per year. Artemisinin, a naturally occurring small molecule that has seen little resistance from malarial parasites, is a valuable weapon in the fight against this disease. Several easily accessible artemisinin derivatives, including artesunate and artemether, display potent antimalarial activity against drug-resistant malaria strains; however, the global supply of artemisinin from natural sources alone remains highly inconsistent and unreliable. As a result, several approaches to artemisinin production have been developed, spanning areas such as total synthesis, flow chemistry, synthetic biology, and semi-synthesis. This review highlights achievements in all areas, in addition to the interplay between synthetic biology and synthetic chemistry that has fueled the recent industrial-scale production of artemisinin.

We report the enantiospecific total synthesis of (+)-tubingensin A. Our synthesis features an aryne cyclization to efficiently introduce the vicinal quaternary stereocenters of the natural product and proceeds in only nine steps (longest linear sequence) from known compounds.

We report the enantiospecific total synthesis of (+)-tubingensin A. Our synthesis features an aryne cyclization to efficiently introduce the vicinal quaternary stereocenters of the natural product and proceeds in only nine steps (longest linear sequence) from known compounds.

Benzoxaborole derivatives are prepared from formylphenylboronic acid derivatives (I) utilizing Baylis-Hillman reaction [cf.

Herein we describe a brief account of betulin and betulinic acid: two natural products isolated from birch bark, their chemical modifications and further biological/medicinal applications.

2-Formylphenylboronic acids upon reaction with activated olefins such as acrylates, methyl vinyl ketone, and acrylonitrile, etc. provide functionalized benzoboroxoles. The corresponding homologated benzoboroxoles were synthesized via the reaction of 2-formylphenylboronic acids with α-bromomethylacrylates.

Correction for ‘Synthetic chemistry fuels interdisciplinary approaches to the production of artemisinin’ by Michael A. Corsello et al., Nat. Prod. Rep., 2015, DOI: 10.1039/c4np00113c.