Elsevier

Tetrahedron Letters

Volume 46, Issue 44, 31 October 2005, Pages 7527-7529
Tetrahedron Letters

Asymmetric synthesis of all the stereoisomers of tarchonanthuslactone

https://doi.org/10.1016/j.tetlet.2005.08.164Get rights and content

Abstract

We describe herein an efficient synthesis of all the four stereoisomers of tarchonanthuslactone from (R)-3-hydroxy butanoate, easily prepared from l-threonine. The approach involves the use of a β,γ-unsaturated δ-lactone as an intermediate, obtained via a Kulinkovich reaction followed by a ring-closing metathesis strategy.

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Acknowledgements

We thank CSIR for a research Grant to V.K.S. and research fellowships to S.B. and S.S.

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