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Asymmetric Total Synthesis of (+)‐Neooxazolomycin Using a Chirality‐Transfer Strategy
Author(s) -
Kim Jae Hyun,
Kim Illan,
Song Yeonghun,
Kim Min Jung,
Kim Sanghee
Publication year - 2019
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.201906158
Subject(s) - stereocenter , chirality (physics) , intramolecular force , aldol reaction , kinetic resolution , natural product , total synthesis , serine , chemistry , stereochemistry , derivative (finance) , enantioselective synthesis , combinatorial chemistry , catalysis , organic chemistry , physics , chiral symmetry breaking , quantum mechanics , quark , financial economics , nambu–jona lasinio model , economics , enzyme
The total synthesis of (+)‐neooxazolomycin was achieved from the amino‐acid d ‐serine. The efficiency of this approach is derived from the use of principles of memory of chirality and dynamic kinetic resolution in the intramolecular aldol reaction of a serine derivative to build the densely functionalized lactam framework and to install three contiguous stereocenters. The key intermediate was readily elaborated to the target natural product.