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Total Synthesis of (+)‐Exiguolide
Author(s) -
Kwon Min Sang,
Woo Sang Kook,
Na Seong Wook,
Lee Eun
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200705018
Subject(s) - olefin metathesis , total synthesis , ring closing metathesis , stereochemistry , closing (real estate) , ring (chemistry) , prins reaction , chemistry , olefin fiber , sponge , metathesis , computer science , organic chemistry , political science , biology , botany , catalysis , law , polymerization , polymer
The unique 16‐membered macrolide (+)‐exiguolide ( 1 ) was the target of a total synthesis featuring radical and Prins cyclizations of β‐alkoxyacrylates, along with ring‐closing olefin metathesis. The structure incorporates two cis ‐2,6‐disubstituted oxane rings where one of the rings has an exocyclic enoate group. The successful synthesis of 1 , isolated from a marine sponge, led to the unambiguous determination of its absolute stereochemistry.