Issue 8, 2011
From the journal:

Organic & Biomolecular Chemistry

Total synthesis of the Amaryllidaceae alkaloid clivonine†

Helmut Haning,ab   Carles Giró-Mañas,c   Victoria L. Paddock,c   Christian G. Bochet,db   Andrew J. P. White,c   Gerald Bernardinelli,b   Inderjit Mann,e   Wolfang Oppolzer‡b  and  Alan C. Spivey*cb  

* Corresponding authors

a Bayer Schering Pharma AG, Müllerstr. 178, Berlin, Germany

b Department of Organic Chemistry, University of Geneva, 30, Quai Ernest Ansermet, Geneva 4, Switzerland

c Department of Chemistry, Imperial College London, South Kensington campus, London, UK
E-mail: a.c.spivey@imperial.ac.uk
Fax: (+) 44 (0)20 75945841
Tel: (+) 44 (0)20 75945841

d Department of Chemistry, University of Fribourg, 9 Ch. du Musee, Fribourg, Switzerland

e GSK Tonbridge, Old Powder Mills, Leigh, Tonbridge, Kent, UK

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

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Article information

DOI
https://doi.org/10.1039/C0OB00895H
Article type
Paper
Submitted
18 Oct 2010
Accepted
13 Jan 2011
First published
02 Mar 2011

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

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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

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