A general approach to the synthesis of butanolides: synthesis of the sex pheromone of the Japanese beetle

…, I Islam, S Chandrasekaran

文献索引：Baskaran, Sundarababu; Islam, Imadul; Chandrasekaran, Srinivasan Journal of Organic Chemistry, 1990 , vol. 55, # 3 p. 891 - 895

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被引用次数: 21

摘要

A variety of substituted y-hydroxy olefiis 1 have been converted to butanolides 4 in very high yield in a three-step sequence involving bromoetherification, elimination, and oxidative cleavage. The key step in the overall transformation is the highly selective oxidative cleavage of enol ethers 3 with PCC under very mild reaction conditions. Application of this methodology has been exemplified in the synthesis of the Japanese beetle pheromone.