A Concise Synthesis of Tashiromine

Alison D. McElhinney; Stephen P. Marsden

doi:10.1055/s-2005-917072

LETTER

A Concise Synthesis of Tashiromine

Alison D. McElhinney, Stephen P. Marsden*
School of Chemistry, University of Leeds, Leeds LS2 9JT, UK
Fax: +44(114)3436465; e-Mail: s.p.marsden@leeds.ac.uk;

Abstract

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Abstract

A concise (six-step) synthesis of the indolizidine alkaloid tashiromine (1) has been achieved. Olefin cross-metathesis was used to prepare a key functionalised allylsilane, which subsequently underwent electrophile-induced ring-closure to establish the bicyclic framework with complete control of stereochemistry.

Key words

alkaloids - cross-metathesis - cyclisation - iminium - organosilicon

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References

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