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Evaluation of Diene Hierarchies for Diels–Alder Reactions En Route to Xestocyclamine A: Elaboration of an Ansa Bridge by B ‐Alkyl Suzuki Macrocyclization
Author(s) -
Gag Alexandre,
Danishefsky Samuel J.
Publication year - 2002
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 - 10.1002/1521-3773(20020503)41:9<1581::aid-anie1581>3.0.co;2-f
Subject(s) - alkyl , diene , chemistry , suzuki reaction , bridge (graph theory) , elaboration , diels–alder reaction , amine gas treating , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , aryl , biology , philosophy , natural rubber , humanities , anatomy
A double Michael addition of amine 2 to 1 was a key reaction in the synthesis of the isoquinuclidine core 4 of xestocyclamine A, a protein kinase C inhibitor. The first ansa bridge was formed efficiently by a B ‐alkyl Suzuki coupling in 3 . TBDPS = tert ‐butyldiphenylsilyl; Ts = p ‐toluenesulfonyl.