Benzannulation of indoles to carbazoles and its applications for syntheses of carbazole alkaloids

Xiaojian Zheng; Leiyang Lv; Shenglin Lu; Wenxiao Wang; Zhiping Li

doi:10.1021/ol5025053

Benzannulation of indoles to carbazoles and its applications for syntheses of carbazole alkaloids

Org Lett. 2014 Oct 3;16(19):5156-9. doi: 10.1021/ol5025053. Epub 2014 Sep 15.

Authors

Xiaojian Zheng¹, Leiyang Lv, Shenglin Lu, Wenxiao Wang, Zhiping Li

Affiliation

¹ Department of Chemistry, Renmin University of China , Beijing 100872, China.

PMID: 25222652
DOI: 10.1021/ol5025053

Abstract

A novel and efficient method for the benzannulation of indoles to carbazoles is reported. γ-Carbonyl tert-butylperoxide is applied as a new diene building block for the π-extension of simple indoles. The synthetic utility of this method is demonstrated by concise and selective total syntheses of naturally occurring carbazole alkaloids, olivacine, and asteropusazole A.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemical synthesis*
Alkaloids / chemistry
Carbazoles / chemical synthesis*
Carbazoles / chemistry
Ellipticines / chemical synthesis*
Ellipticines / chemistry
Indoles / chemistry*
Molecular Structure
Stereoisomerism

Substances

Alkaloids
Carbazoles
Ellipticines
Indoles
asteropusazole A
olivacine