Organic letters

A Concise Total Synthesis of Pyrovellerolactone Using a Rhodium-Catalyzed [(3+ 2)+ 2] Carbocyclization Reaction

PA Evans, PA Inglesby, K Kilbride

文献索引：Evans, P. Andrew; Inglesby, Phillip A.; Kilbride, Kathryn Organic Letters, 2013 , vol. 15, # 8 p. 1798 - 1801

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被引用次数: 21

摘要

A concise and highly convergent three-step total synthesis of the lactarane natural product, pyrovellerolactone, is described. The key step involves a regio-and diastereoselective rhodium-catalyzed [(3+ 2)+ 2] carbocyclization of an alkenylidenecyclopropane with a 4- hydroxybut-2-ynoate followed by an in situ intramolecular lactonization to generate the tricyclic core in a single operation. This represents the first example of a higher-order [3+ 2 ...