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Total synthesis of the lycorenine-type amaryllidaceae alkaloid (+/-)-clivonine via a biomimetic ring-switch from a lycorine-type progenitor.

Type of publication Peer-reviewed
Publikationsform Original article (peer-reviewed)
Publication date 2010
Author Giró Mañas Carles, Paddock Victoria L, Bochet Christian G, Spivey Alan C, White Andrew J P, Mann Inderjit, Oppolzer Wolfgang,
Project Photons in organic synthesis
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Original article (peer-reviewed)

Journal Journal of the American Chemical Society
Volume (Issue) 132(14)
Page(s) 5176 - 8
Title of proceedings Journal of the American Chemical Society
DOI 10.1021/ja910184j

Abstract

A fully diastereoselective total synthesis of the lycorenine-type Amaryllidaceae alkaloid (+/-)-clivonine (19) is reported via a route that employs for the first time a biomimetic ring-switch from a lycorine-type progenitor, thereby corroborating experimentally the biogenetic hypothesis first expounded for these compounds by Barton in 1960.
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