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Total Synthesis of Umuravumbolide
Author(s) -
Shekhar Vanam,
Reddy Dorigondla Kumar,
Venkateswarlu Yenamandra
Publication year - 2012
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200078
Subject(s) - chemistry , kinetic resolution , total synthesis , stereoselectivity , sharpless epoxidation , hydrolysis , stereochemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis
A simple and efficient stereoselective total synthesis of (+)‐umuravumbolide ( 1b ) and (−)‐deacetylumuravumbolide ( 1a ) starting from commercially available pentanal is described. The synthesis involves Sharpless asymmetric epoxidation, Jacobsen 's hydrolytic kinetic resolution (HKR), and the Yamaguchi oxirane opening as key steps ( Scheme 2 ).