Synlett 2005(16): 2528-2530  
DOI: 10.1055/s-2005-917072
LETTER
© Georg Thieme Verlag Stuttgart · New York

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;
Further Information

Publication History

Received 12 August 2005
Publication Date:
21 September 2005 (online)

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.

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Cost of starting materials from Aldrich, 2005: 4-pentynyl-oxytetrahydropyran £1430 per mol and iodomethyltri-methylsilane £293 per mol; allyltrimethylsilane £211 per mol.