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Total Syntheses of Dendrodolides A, B, and E
Author(s) -
Mohapatra Debendra K.,
Pulluri Karthik,
Bhimireddy Eswar,
Reddy D. Prabhakar,
Yadav Jhillu S.
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201402126
Subject(s) - chemistry , yield (engineering) , epoxide , ring closing metathesis , total synthesis , stereochemistry , metathesis , alcohol , salt metathesis reaction , ring (chemistry) , enantioselective synthesis , organic chemistry , catalysis , materials science , polymer , metallurgy , polymerization
Convergent total syntheses of dendrodolides A, B, and E comprising 12‐membered macrolactones are described. The syntheses of dendrodolides A and B were accomplished in 11 linear steps with 24 % and 25 % overall yield, respectively, starting from commercially available homoallyl alcohol 19 and enantiomerically pure epoxide 20 . Dendrodolide E was subsequently obtained from dendrodolides A or B in 81 % yield by treatment with BCl 3 . Key steps were Maruoka asymmetric allylation, Corey‐Chaykovsky reaction, Yamaguchi esterification, and ring‐closing metathesis.