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

Mañas, Carles Giró; Paddock, Victoria L.; Bochet, Christian G.; Spivey, Alan C.; White, Andrew J. P.; Mann, Inderjit; Oppolzer, Wolfgang

doi:10.1021/ja910184j

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Journal article

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

Mañas, Carles Giró Department of Chemistry, Imperial College London, UK
Paddock, Victoria L. Department of Chemistry, Imperial College London, UK
Bochet, Christian G. Department of Chemistry, UniVersity of Fribourg, Switzerland - Department of Organic Chemistry, University of Geneva, Switzerland
Spivey, Alan C. Department of Chemistry, Imperial College London, UK - Department of Organic Chemistry, University of Geneva, Switzerland
White, Andrew J. P. Department of Chemistry, Imperial College London, UK
Mann, Inderjit Department of Organic Chemistry, University of Geneva, Switzerland
Oppolzer, Wolfgang Department of Organic Chemistry, University of Geneva, Switzerland

17.03.2010

Published in:

Journal of the American Chemical Society. - 2010, vol. 132, no. 14, p. 5176–5178

English A fully diastereoselective total synthesis of the lycorenine-type Amaryllidaceae alkaloid (±)-clivonine 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.

Faculty

Faculté des sciences et de médecine

Department

Département de Chimie

Language