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A Short and Flexible Synthetic Approach to the Naturally Occurring Racemic Neoclausenamide and Its Analogs
Author(s) -
Dai Xijie,
Huang Peiqiang
Publication year - 2012
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201200660
Subject(s) - chemistry , stereocenter , diastereomer , conjugate , stereochemistry , tandem , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , mathematical analysis , materials science , mathematics , composite material
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 of N ‐Boc‐pyrrol‐2(5 H )‐one 5 ( dr =10:1). Remarkably, the skeleton of neoclausenamide, namely 8a , an analog of neoclausenamide, was built in just two steps with all the four stereogenic centers (relative stereochemistry) established correctly and in excellent diastereoselectivities.