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Total Synthesis of (+)‐Concanamycin F
Author(s) -
Paterson Ian,
Doughty Victoria A.,
McLeod Malcolm D.,
Trieselmann Thomas
Publication year - 2000
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(20000403)39:7<1308::aid-anie1308>3.0.co;2-7
Subject(s) - aldol reaction , protein subunit , chemistry , total synthesis , stereochemistry , boron , combinatorial chemistry , biochemistry , catalysis , organic chemistry , gene
The choice of protecting groups proved imperative for successful macrocyclization in the total synthesis of the 18‐membered macrolide concanamycin F ( 1 ), which is a potent inhibitor of vacuolar (H + ) ATPases. A C 14 – C 22 subunit was prepared with complete stereocontrol by using asymmetric, boron‐mediated, aldol reactions with appropriate chiral ketones. Other key steps included a copper( I )‐mediated, Liebeskind cross‐coupling and a Mukaiyama aldol reaction for subunit assembly.