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Asymmetric Total Synthesis of (−)‐Cladospolide B
Author(s) -
WANG WenKuan,
ZHANG JiYong,
HE JinMei,
TANG ShiBing,
WANG XiaoLei,
SHE XueGong,
PAN XinFu
Publication year - 2008
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.200890197
Subject(s) - chemistry , enantioselective synthesis , total synthesis , stereochemistry , dihydroxylation , mitsunobu reaction , ring closing metathesis , sharpless epoxidation , ring (chemistry) , metathesis , salt metathesis reaction , sharpless asymmetric dihydroxylation , organic chemistry , catalysis , polymer , polymerization
An enantioselective total synthesis of (−)‐cladospolide B was described. The key steps in this synthesis include(a) a Sharpless asymmetric dihydroxylation to elaborate syn diol at C‐4 and C‐5 positions; (b) a Mitsunobu esterification to reverse the configuration at C‐11 from ( S ) to ( R ); and (c) a ring‐closing metathesis to access the 12‐membered macrocyclic ring.