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Total Synthesis of Sacrolide A by Following a Nozaki‐Hiyama‐Kishi Macrocyclization Strategy
Author(s) -
Jena Bighnanshu K.,
Reddy Aedula Vishnu V.,
Mohapatra Debendra K.
Publication year - 2016
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.201500537
Subject(s) - chemistry , kinetic resolution , stereoselectivity , intramolecular force , yield (engineering) , stereochemistry , total synthesis , lactone , hydrolysis , oxylipin , enantioselective synthesis , organic chemistry , catalysis , enzyme , materials science , metallurgy
The stereoselective total synthesis of oxylipin macrolide (+)‐sacrolide A was achieved in a 13 longest linear step sequence with 12.1 % overall yield. The key reactions are Jacobsen′s hydrolytic kinetic resolution, Sharpless asymmetric epoxidation, Yamaguchi esterification and intramolecular Nozaki–Hiyama–Kishi (NHK) macrocyclization to construct the required 14‐membered lactone.