Elsevier

Tetrahedron Letters

Volume 41, Issue 44, 28 October 2000, Pages 8569-8572
Tetrahedron Letters

Synthetic studies on the salicylihalamides: macrolactone formation via ring closing metathesis versus macrolactonization

https://doi.org/10.1016/S0040-4039(00)01420-9Get rights and content

Abstract

Two routes to the unusual 12-membered unsaturated benzolactone of the highly cytotoxic marine metabolites the salicylihalamides are presented. The first involves an RCM step to construct the C9C10 alkene bond and this provided the model macrolactones 9 and 10 in a ratio of 77:23, respectively. An alternative route involved a Stille coupling to construct the C8C9 bond followed by a macrolactonization to give the lactones 9 and 10 in a ratio of 96:4.

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Acknowledgements

We thank the Australian Research Council for financial support.

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