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Total Synthesis of Bafilomycin A 1
Author(s) -
Kleinbeck Florian,
Carreira Erick M.
Publication year - 2009
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.200804645
Subject(s) - bafilomycin , enyne , aldehyde , key (lock) , computer science , coupling (piping) , chemistry , combinatorial chemistry , stereochemistry , catalysis , organic chemistry , engineering , operating system , mechanical engineering , apoptosis , biochemistry , autophagy
A convergent synthesis of bafilomycin A 1 (see structure) is presented, and relies on the Zn(OTf) 2 ‐mediated diastereoselective addition of alkynes to aldehydes. The coupling of a complex enyne with a sensitive aldehyde in the key step, in combination with a novel strategy for a chemoselective trans ‐reduction of the enyne, establishes an alternative to standard palladium‐catalyzed cross‐coupling strategies for the formation of 1,3‐dienes.