Biomimetic collective total synthesis of bioactive carbazole alkaloids indizoline, mafaicheenamine A, claulamine A, claulansine A, and the proposed claulamine E

TitleBiomimetic collective total synthesis of bioactive carbazole alkaloids indizoline, mafaicheenamine A, claulamine A, claulansine A, and the proposed claulamine E
Publication TypeJournal Article
Year of Publication2016
AuthorsMarkad, SB, Argade, NP
JournalJournal of Organic Chemistry
Volume81
Issue12
Pagination5222-5227
Date PublishedJUN
ISSN0022-3263
Abstract

The common precursor 1-methoxy-2-prenyl-3-carbomethoxycarbazole was synthesized from dimethyl indolylmethylenesuccinate in four steps. Well-planned reductive and/or oxidative transformations and intramolecular cyclizations were performed on a pivotal common precursor to accomplish collective first total synthesis of titled natural products and proposed Claulamine E. Burgess reagent induced formation of kinetically controlled product Claulamine A, and intramolecular cyclizations to form bicyclic claulansine A were the key reactions. An alternatively attempted synthesis failed to provide the structural isomer of proposed Claulamine E.

DOI10.1021/acs.joc.6b00702
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)4.785
Divison category: 
Organic Chemistry