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Total synthesis of the Amaryllidaceae alkaloid clivonine.

Type of publication Peer-reviewed
Publikationsform Original article (peer-reviewed)
Publication date 2011
Author Haning Helmut, Giró-Mañas Carles, Paddock Victoria L, Bochet Christian G, White Andrew J P, Bernardinelli Gerald, Mann Inderjit, Oppolzer Wolfang, Spivey Alan C,
Project Photons in organic synthesis
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Original article (peer-reviewed)

Journal Organic & biomolecular chemistry
Volume (Issue) 9(8)
Page(s) 2809 - 20
Title of proceedings Organic & biomolecular chemistry
DOI 10.1039/c0ob00895h

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.
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