Diversity oriented convergent access for collective total synthesis of bioactive multifunctional carbazole alkaloids: synthesis of carbazomycin A, carbazomycin B, hyellazole, chlorohyellazole, and clausenaline D

TitleDiversity oriented convergent access for collective total synthesis of bioactive multifunctional carbazole alkaloids: synthesis of carbazomycin A, carbazomycin B, hyellazole, chlorohyellazole, and clausenaline D
Publication TypeJournal Article
Year of Publication2014
AuthorsMarkad, SB, Argade, NP
JournalOrganic Letters
Volume16
Issue20
Pagination5470-5473
Date PublishedOCT
Type of ArticleArticle
ISSN1523-7060
Abstract

Facile syntheses of imperative carbazole alkaloids carbazomycin A, carbazomycin B, hyellazole, chlorohyellazole, and clausenaline D have been demonstrated starting from readily available Boc-protected 3-formylindole and dimethyl maleate. The suitably substituted aromatic rings have been designed comprising three/four significant C-C bond forming reactions. The competent Wittig reaction, selective monoalkylations, one-pot regioselective Weinreb amide formation and Boc-deprotection, well designed Grignard reactions, dehydrative intramolecular cyclizations, and Baeyer-Villiger rearrangement of aromatic aldehydes were the main features.

DOI10.1021/ol502721r
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

6.732

Divison category: 
Organic Chemistry