Concise approach to pyrrolizino[1, 2-b]indoles from indole-derived donor–acceptor cyclopropanes. Issue 66 (28th June 2016)

• Record Type: Journal Article
• Authors: Villemson, Elena V.; Budynina, Ekaterina M.; Ivanova, Olga A.; Skvortsov, Dmitriy A.; Trushkov, Igor V.; Melnikov, Mikhail Ya.
• Is Part Of: RSC advances. Volume 6:Issue 66(2016)
• Page Start: 62014
• Page End: 62018
• Publication Date: 2016-06-28
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c6ra11233a
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : A direct approach to previously unexplored pyrrolizidino[1, 2- b ]indole system from indole-derived donor–acceptor cyclopropanes based on a sequence of three synthetic steps was developed. Abstract : Developed here is a direct three-step approach to a previously unexplored pyrrolizino[1, 2- b ]indole system based on a sequence of three synthetic steps: (a) one-pot azide ion promoted ring opening of the indole-derived donor–acceptor cyclopropane and Krapcho dealkoxycarbonylation; (b) Vilsmeier–Haack formylation; (c) tandem Staudinger/intramolecular aza-Wittig reaction and reductive cyclization realized in a one pot fashion.