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Enantioselective Synthesis of Oasomycin A, Part I: Synthesis of the C1–C12 and C13–C28 Subunits
Author(s) -
Evans David A.,
Nagorny Pavel,
McRae Kenneth J.,
Reynolds Dominic J.,
Sonntag LouisSebastian,
Vounatsos Filisaty,
Xu Risheng
Publication year - 2007
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.200603653
Subject(s) - enantioselective synthesis , acylation , amide , aldol reaction , content (measure theory) , key (lock) , chemistry , computer science , stereochemistry , total synthesis , combinatorial chemistry , organic chemistry , catalysis , mathematics , mathematical analysis , computer security
Putting the pieces together : The total synthesis of the natural macrolide oasomycin A has been realized. Key fragment couplings include an anti ‐Felkin selective aldol addition (green), Kociensky–Julia olefinations (red), and competitive Weinreb amide acylation reaction (blue). The utility of the 4,5‐diphenyloxazole as a carboxy surrogate and the late‐stage macrolactonization affording the 42‐membered macrocycle of oasomycin A are also described.