Premium
Rapid Two‐Directional Synthesis of the F–J Fragment of the Gambieric Acids by Iterative Double Ring‐Closing Metathesis
Author(s) -
Clark J. Stephen,
Kimber Marc C.,
Robertson Jerod,
McErlean Christopher S. P.,
Wilson Claire
Publication year - 2005
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.200501925
Subject(s) - ring closing metathesis , fragment (logic) , closing (real estate) , salt metathesis reaction , metathesis , chemistry , ring (chemistry) , sequence (biology) , stereochemistry , hydroboration , mathematics , organic chemistry , algorithm , catalysis , biochemistry , political science , law , polymerization , polymer
D ‐glucal is the starting point for the efficient synthesis of the F–J fragment of the gambieric acids (see scheme). The H‐ring diol was subjected to double two‐directional alkynyl ether formation, carbocupration ring‐closing metathesis, and hydroboration. The tricyclic G–I diol was then converted into the F–J fragment by a sequence that involves another double two‐directional ring‐closing metathesis reaction.