Semisynthesis of (+)- and (−)-goniomitine from (−)- and (+)-vincadifformine

The first biomimetic semisynthesis of goniomitine has been accomplished in nine steps with 11% overall yield starting from vincadifformine. Natural (−)- and unnatural (+)-goniomitine were prepared from (+)- and (−)-vincadifformine, respectively. The evaluation of the antiproliferative effect of both...

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Bibliographic Details
Published in:Tetrahedron 2013-02, Vol.69 (5), p.1622-1627
Main Authors: Lewin, Guy, Bernadat, Guillaume, Aubert, Geneviève, Cresteil, Thierry
Format: Article
Language:English
Subjects:
Antiproliferatives
Aspidospermane
Biomimetics
Chemical Sciences
Derivatives
Enantiomers
Goniomitine
Indole alkaloids
Organic chemistry
Semisynthesis
Tetrahedrons
Vincadifformine
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Summary:The first biomimetic semisynthesis of goniomitine has been accomplished in nine steps with 11% overall yield starting from vincadifformine. Natural (−)- and unnatural (+)-goniomitine were prepared from (+)- and (−)-vincadifformine, respectively. The evaluation of the antiproliferative effect of both enantiomers proved unnatural (+)-goniomitine to be more potent, but this enantiomer as well as some close derivatives displayed a moderate activity only. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.11.084