title: Enantioselective total synthesis of desbromoarborescidines A-C and the formal synthesis of (S)-deplancheine.
abstract: Starting from Boc-protected tryptamine and (S)-tetrahydro-5-oxo-2-furancarboxylic acid, facile enantioselective total synthesis of desbromoarborescidines A-C and the formal synthesis of (S)-deplancheine have been accomplished via a common intermediate (S)-indolo[2,3-a]quinolizine. Synthesis of enantiomerically pure (S)-acetoxyglutarimide, stereoselective reductive intramolecular cyclization, hydroxyl group-assisted in situ N-Boc-deprotection, selective deoxygenation of the xanthate ester, and lactam hydrolysis followed by an appropriate exchange of nitrogen regioselectivity in intramolecular cyclization were the decisive steps.
authors.affiliation: Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India.
authors.forename: Pravat
authors.initials: P
authors.lastname: Mondal
authors.forename: Narshinha P
authors.initials: NP
authors.lastname: Argade
mesh_terms: D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D026121:Indole Alkaloids; C496494:deplancheine; C506148:desbromoarborescidine A; C506149:desbromoarborescidine C