A Concise Synthesis of Tashiromine

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.

alkaloids - cross-metathesis - cyclisation - iminium - organosilicon

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21

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