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Enantioselective Synthesis of Oasomycin A, Part III: Fragment Assembly and Confirmation of Structure
Author(s) -
Evans David A.,
Nagorny Pavel,
McRae Kenneth J.,
Sonntag LouisSebastian,
Reynolds Dominic J.,
Vounatsos Filisaty
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.200603652
Subject(s) - enantioselective synthesis , fragment (logic) , acylation , aldol reaction , amide , key (lock) , chemistry , content (measure theory) , stereochemistry , computer science , combinatorial chemistry , organic chemistry , programming language , 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.