Novel fragmentation reaction of correolide |
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| Authors: | Bao Jianming Baker Robert K Doss George A Kayser Frank Kotliar Andrew Miao Shouwu Parsons William H Rupprecht Kathleen M |
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| Institution: | Department of Medicinal Chemistry, Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065, USA. bao_jianming@merck.com |
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| Abstract: | reaction: see text] Pentacyclic triterpenoid natural product correolide (1) was converted to ketone 2 via ozonolysis. An unusual fragmentation reaction of ketone 2 with LiCl was discovered. This reaction is general among several similar substrates examined and appears to be specific for the correolide-type E-ring structure (ketone). A mechanism involving a retroaldol reaction, a nucleophilic opening of the epoxide, and a subsequent acetoxy elimination reaction was proposed. |
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