Issue 8, 2011

Total synthesis of the Amaryllidaceae alkaloid clivonine

Abstract

Two syntheses of the Amaryllidaceae alkaloid clivonine (1) are described. Both employ previously reported 7-arylhydrindane 6 as an intermediate but differ in the method employed for subsequent introduction of what becomes the ring-B lactonecarbonyl carbon (C7). The synthesis featuring a Bischler–Napieralski reaction for this transformation constitutes the first asymmetric synthesis of natural (+)-clivonine. Crystal structures for compounds (±)-13, (±)-16, (−)-20 and (±)-28 are also reported.

Graphical abstract: Total synthesis of the Amaryllidaceae alkaloid clivonine

Supplementary files

Article information

Article type
Paper
Submitted
18 Oct 2010
Accepted
13 Jan 2011
First published
02 Mar 2011

Org. Biomol. Chem., 2011,9, 2809-2820

Total synthesis of the Amaryllidaceae alkaloid clivonine

H. Haning, C. Giró-Mañas, V. L. Paddock, C. G. Bochet, A. J. P. White, G. Bernardinelli, I. Mann, W. Oppolzer and A. C. Spivey, Org. Biomol. Chem., 2011, 9, 2809 DOI: 10.1039/C0OB00895H

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements