Issue 8, 2016

Enantioselective synthesis of Iboga alkaloids and vinblastine via rearrangements of quaternary ammoniums

Abstract

An efficient and novel strategy for the enantioselective syntheses of various iboga alkaloids has been developed. The salient features include a gold-catalyzed oxidation of a terminal alkyne followed by cyclization, a Stevens rearrangement and a tandem sequence that combines the gold-catalyzed oxidation, cyclization and [1,2]-shift. The catharanthine analogs provided by our approach were further converted to the vinca alkaloid vinblastine and its analogs, which confirmed the remarkable sensitivity of the cytotoxicity to the C20′ substituent of vinblastine.

Graphical abstract: Enantioselective synthesis of Iboga alkaloids and vinblastine via rearrangements of quaternary ammoniums

Supplementary files

Article information

Article type
Edge Article
Submitted
29 Feb 2016
Accepted
13 May 2016
First published
16 May 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2016,7, 5530-5536

Enantioselective synthesis of Iboga alkaloids and vinblastine via rearrangements of quaternary ammoniums

Y. Zhang, Y. Xue, G. Li, H. Yuan and T. Luo, Chem. Sci., 2016, 7, 5530 DOI: 10.1039/C6SC00932H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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