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Issue 8, 2011
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Total synthesis of the Amaryllidaceae alkaloid clivonine

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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


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

Org. Biomol. Chem., 2011,9, 2809-2820
Article type
Paper

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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