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Stereocontrolled Total Synthesis of (+)‐Streptazolin by a Palladium‐Catalyzed Reductive Diyne Cyclization
Author(s) -
Trost Barry M.,
Chung Cheol K.,
Pinkerton Anthony B.
Publication year - 2004
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.200460058
Subject(s) - alkyne , total synthesis , palladium , key (lock) , chemistry , catalysis , computer science , combinatorial chemistry , organic chemistry , operating system
(+)‐Streptazolin synthesis revisited: The key reaction in the 11‐step total synthesis of (+)‐streptazolin ( 3 ), which starts from D ‐mannitol diacetonide, is the palladium‐catalyzed reductive cyclization of two alkyne arms in 1 to provide the desired 1,3‐diene 2 with the correct defined geometry. TBS= tert ‐butyldimethylsilyl.