Concise synthesis of (S,S)-(+)-dehydrohomoancepsenolide |
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Authors: | Fürstner A Dierkes T |
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Affiliation: | Max-Planck-Institut für Kohlenforschung, D-45470 Mülheim/Ruhr, Germany. fuerstner@mpi-muelheim.mpg.de |
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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 (PCy(3))(2)Cl(2)Ru=CHPh. Dimerization of the resulting butenolide 11 is then achieved via alkyne metathesis using (tBuO)(3)W&tbd1;CCMe(3) as the catalyst. A Lindlar reduction completes this synthesis which delivers product 3 in only five steps with an overall yield of 25%. |
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