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A Short and Efficient Synthesis of Neodysiherbaine A by Using Catalytic Oxidative Cyclization
Author(s) -
Donohoe Timothy J.,
Winship Paul C. M.,
Tatton Matthew R.,
Szeto Peter
Publication year - 2011
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.201102525
Subject(s) - chemistry , stereochemistry , stereocenter , combinatorial chemistry , alkene , moiety , total synthesis , kainate receptor , ampa receptor , catalysis , enantioselective synthesis , glutamate receptor , organic chemistry , receptor , biochemistry
To the point : The synthesis of the title compound was achieved with 24 % overall yield through a sequence that has just seven linear steps (see scheme). Key points are the facial selectivity displayed by an oxocarbenium ion derived from a ribopyranose system and an osmium‐catalyzed oxidative cyclization that is compatible with several acid‐sensitive groups.