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A Short and Flexible Synthetic Approach to the Naturally Occurring Racemic Neoclausenamide and Its Analogs 被引量:3

A Short and Flexible Synthetic Approach to the Naturally Occurring Racemic Neoclausenamide and Its Analogs
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摘要 A novel strategy was developed for a rapid access to the naturally occurring racemic neoclausenamide and its analogs, which featured a highly erythro-selective vinylogous Mukaiyama type reaction (dr= 12:1) and a highly diastereoselective tandem conjugate addition-Davis oxidation ofN-Boc-pyrrol-2(5H)-one 5 (dr= 10:1). Remarka- bly, the skeleton of neoclausenamide, namely 8n, an analog of neoclausenamide, was built in just two steps with all the four stereogenic centers (relative stereochemistry) established correctly and in excellent diastereoselectivities. A novel strategy was developed for a rapid access to the naturally occurring racemic neoclausenamide and its analogs, which featured a highly erythro-selective vinylogous Mukaiyama type reaction (dr= 12:1) and a highly diastereoselective tandem conjugate addition-Davis oxidation ofN-Boc-pyrrol-2(5H)-one 5 (dr= 10:1). Remarka- bly, the skeleton of neoclausenamide, namely 8n, an analog of neoclausenamide, was built in just two steps with all the four stereogenic centers (relative stereochemistry) established correctly and in excellent diastereoselectivities.
出处 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2012年第9期1953-1956,共4页 中国化学(英文版)
关键词 (±)-neoclausenamide vinylogous Mukaiyama reaction tandem reaction stereoselective synthesis pyrrol-2(SH)-one (±)-neoclausenamide, vinylogous Mukaiyama reaction, tandem reaction, stereoselective synthesis,pyrrol-2(SH)-one
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