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Total Synthesis of (+)‐Seimatopolide A
Author(s) -
Raji Reddy Chada,
Rao Nagavaram Narsimha,
Reddy Motatipally Damoder
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200732
Subject(s) - chemistry , total synthesis , enantioselective synthesis , dihydroxylation , sharpless asymmetric dihydroxylation , metathesis , stereochemistry , natural product , ring closing metathesis , salt metathesis reaction , stereoisomerism , organic chemistry , molecule , catalysis , polymer , polymerization
The first enantioselective total synthesis of a polyhydroxylated macrolide, (+)‐seimatopolide A, was achieved. The key reactions, Sharpless asymmetric dihydroxylation, Yamaguchi esterification, and ring‐closing metathesis, provided easy access to the target molecule from L ‐aspartic acid. Further, the absolute stereochemistry of the natural product has also been revised.