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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 (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%.
