Concise Synthesis of (S,S)-(+)-Dehydrohomoancepsenolide

Fürstner, Alois; Dierkes, Thorsten

doi:10.1021/ol006122d

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Concise Synthesis of (S,S)-(+)-Dehydrohomoancepsenolide

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Fürstner, Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Dierkes, Thorsten
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Fürstner, A., & Dierkes, T. (2000). Concise Synthesis of (S,S)-(+)-Dehydrohomoancepsenolide. Organic Letters, 2(16), 2463-2465. doi:10.1021/ol006122d.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0024-485F-6

Abstract

A concise total synthesis of the bis-butenolide 3 in optically active form is reported. Key steps are a zinc-mediated “three-component coupling” with formation of dienyne 9 which undergoes ring closing metathesis (RCM) on treatment with (PCy₃)₂Cl₂Ru=CHPh. Dimerization of the resulting butenolide 11 is then achieved via alkyne metathesis using (tBuO)₃WΞCCMe₃ as the catalyst. A Lindlar reduction completes this synthesis which delivers product 3 in only five steps with an overall yield of 25%.