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Amipurimycin: Total Synthesis of the Proposed Structures and Diastereoisomers
Author(s) -
Wang Shengyang,
Sun Jiansong,
Zhang Qingju,
Cao Xin,
Zhao Yachen,
Tang Gongli,
Yu Biao
Publication year - 2018
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.201800169
Subject(s) - diastereomer , stereoselectivity , stereochemistry , epimer , nucleoside , chemistry , aldol reaction , aldol condensation , glycosylation , combinatorial chemistry , organic chemistry , catalysis , biochemistry
Abstract The proposed diastereoisomers ( 1 a – d ) together with their C8′‐epimers ( 1 e – h ) of amipurimycin, a unique antifungal peptidyl nucleoside antibiotic, have been synthesized for the first time. The synthetic approach is efficient and stereodivergent, and features a stereoselective aldol condensation to build the branched C9 sugar amino acid skeleton and a regio‐ and stereocontrolled gold(I)‐catalyzed N‐glycosylation to furnish the purine nucleoside. Analysis of the NMR data suggests that the previously assigned configuration of the tertiary C3′ in amipurimycin should be of opposite configuration.