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Total Synthesis of Pinnatoxin A
Author(s) -
Nakamura Seiichi,
Kikuchi Fumiaki,
Hashimoto Shunichi
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.200802729
Subject(s) - cycloisomerization , enyne , ruthenium , imine , chemistry , total synthesis , ring (chemistry) , dehydration , methylene , lactone , catalysis , stereochemistry , medicinal chemistry , organic chemistry , biochemistry
A familiar ring : A ruthenium‐catalyzed cycloisomerization of an enyne, synthesized by an exo ‐selective Diels–Alder reaction with an α‐methylene lactone as the dienophile, proved to be highly effective for the construction of the 27‐membered carbocycle of pinnatoxin A. The total synthesis was completed upon the formation of the seven‐membered cyclic imine by self‐catalyzed dehydration.