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Total Synthesis of (−)‐Bafilomycin A 1 : Application of Diastereoselective Crotylboration and Methyl Ketone Aldol Reactions
Author(s) -
Scheidt Karl A.,
Tasaka Akihiro,
Bannister Thomas D.,
Wendt Michael D.,
Roush William R.
Publication year - 1999
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/(sici)1521-3773(19990601)38:11<1652::aid-anie1652>3.0.co;2-k
Subject(s) - aldol reaction , methyl ketone , stereoselectivity , ketone , bafilomycin , total synthesis , chemistry , coupling reaction , stereochemistry , aldol condensation , combinatorial chemistry , organic chemistry , catalysis , biochemistry , apoptosis , autophagy
A careful orchestration of protecting groups is an essential requirement for the total synthesis of the macrolide antibiotic bafilomycin A 1 ( 1 ). Key steps were the Suzuki cross‐coupling reaction of two advanced, suitably protected intermediates prior to closure of the macrocycle, as well as a highly stereoselective methyl ketone aldol reaction.