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Synlett 2005(16): 2528-2530
DOI: 10.1055/s-2005-917072
DOI: 10.1055/s-2005-917072
LETTER
© Georg Thieme Verlag Stuttgart · New York
A Concise Synthesis of Tashiromine
Further Information
Received
12 August 2005
Publication Date:
21 September 2005 (online)
Publication History
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.
Key words
alkaloids - cross-metathesis - cyclisation - iminium - organosilicon
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References
Cost of starting materials from Aldrich, 2005: 4-pentynyl-oxytetrahydropyran £1430 per mol and iodomethyltri-methylsilane £293 per mol; allyltrimethylsilane £211 per mol.