Total synthesis of the Amaryllidaceae alkaloid clivonine.

Authors

Helmut Haning
Carles Giró-Mañas
Victoria L Paddock
Christian G Bochet
Andrew J P White
Gerald Bernardinelli
Inderjit Mann
Wolfang Oppolzer
Alan C Spivey

Publication/Presentation Date

4-21-2011

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 lactone carbonyl 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.

Volume

9

Issue

8

First Page

2809

Last Page

2820

ISSN

1477-0539

Published In/Presented At

Haning, H., Giró-Mañas, C., Paddock, V. L., Bochet, C. G., White, A. J., Bernardinelli, G., Mann, I., Oppolzer, W., & Spivey, A. C. (2011). Total synthesis of the Amaryllidaceae alkaloid clivonine. Organic & biomolecular chemistry, 9(8), 2809–2820. https://doi.org/10.1039/c0ob00895h

Disciplines

Medicine and Health Sciences

PubMedID

21365099

Department(s)

Department of Medicine

Document Type

Article