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A series of new thienyl ring containing analogues of nelfinavir and saquinavir with different substitution patterns were synthesized from suitable enantiopure diols. Their inhibitory activity against wild type recombinant HIV-1 protease was evaluated. In general thienyl groups spaced from the core by a methylene group gave products showing IC(50) in the nanomolar range, irrespective of the type and the substitution pattern of the heterocycle. The range of activity of the two most active compounds is substantially maintained or even increased against two commonly selected mutants, under drug pressure, such as V32I and V82A.

Optimized conditions for the catalytic asymmetric dihydroxylation have been applied to thiophene and benzothiophene containing acrylates and crotonates to afford the corresponding diols in good overall yields and good to excellent enantiomeric excess. The products obtained were revealed to be useful intermediates in peptidomimetic synthesis.

Mild thermal reaction of enones with N -(benzofuran-3-yl)iminophosphorane, newly prepared by Staudinger reaction of 3-azidobenzofuran with triphenylphosphine, provides a synthetic en-try to virtually unknown benzo[4,5]furo[3,2- b ]pyridines via a tan-dem aza-Wittig–electrocyclization process. Key words: iminophosphoranes, azides, aza-Wittig, electrocy-clization, benzofuropyridines Small heterocyclic molecules play an important role inmodern pharmaceutical and medicinal chemistry. 1 In par-ticular, benzo[4,5]furopyridines, isosteric of both carbo-lines and dibenzofuran, often display important biologicaland pharmacological activities. 2,3 Benzo[4,5]furo[ c ]pyridines and their tetrahydro deriva-tives are long-known compounds available through vari-ous reported methods. 4 In contrast, the benzo-[4,5]furo[ b ]pyridine congeners remain little known. In-deed, only scant examples of benzo[4,5]furo[2,3- b ]py-ridines were present in the literature 4b,5c,d until two veryrecent papers described the preparation of a variety ofthose tricyclic compounds through the unusual use of insitu generated 2-aminobenzofuran as the crucial interme-diate.

Mild thermal reaction of enones with N -(benzofuran-3-yl)iminophosphorane, newly prepared by Staudinger reaction of 3-azidobenzofuran with triphenylphosphine, provides a synthetic en-try to virtually unknown benzo[4,5]furo[3,2- b ]pyridines via a tan-dem aza-Wittig–electrocyclization process. Key words: iminophosphoranes, azides, aza-Wittig, electrocy-clization, benzofuropyridines Small heterocyclic molecules play an important role inmodern pharmaceutical and medicinal chemistry. 1 In par-ticular, benzo[4,5]furopyridines, isosteric of both carbo-lines and dibenzofuran, often display important biologicaland pharmacological activities. 2,3 Benzo[4,5]furo[ c ]pyridines and their tetrahydro deriva-tives are long-known compounds available through vari-ous reported methods. 4 In contrast, the benzo-[4,5]furo[ b ]pyridine congeners remain little known. In-deed, only scant examples of benzo[4,5]furo[2,3- b ]py-ridines were present in the literature 4b,5c,d until two veryrecent papers described the preparation of a variety ofthose tricyclic compounds through the unusual use of insitu generated 2-aminobenzofuran as the crucial interme-diate.