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

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

doi:10.1021/ja910184j

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

J Am Chem Soc. 2010 Apr 14;132(14):5176-8. doi: 10.1021/ja910184j.

Authors

Carles Giró Mañas¹, Victoria L Paddock, Christian G Bochet, Alan C Spivey, Andrew J P White, Inderjit Mann, Wolfgang Oppolzer

Affiliation

¹ Department of Chemistry, South Kensington Campus, Imperial College London, London SW7 2AZ, UK.

PMID: 20235577
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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amaryllidaceae Alkaloids / chemical synthesis*
Amaryllidaceae Alkaloids / chemistry*
Crystallography, X-Ray
Cyclization
Models, Molecular
Molecular Structure
Phenanthridines / chemistry*
Stereoisomerism

Substances

Amaryllidaceae Alkaloids
Phenanthridines
clivonine
lycorenine
lycorine