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New Synthetic Technology for the Construction of N‐Containing Quinones and Derivatives Thereof: Total Synthesis of Epoxyquinomycin B
Author(s) -
Nicolaou K. C.,
Sugita Kazuyuki,
Baran Phil S.,
Zhong YongLi
Publication year - 2001
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 - 10.1002/1521-3773(20010105)40:1<207::aid-anie207>3.0.co;2-k
Subject(s) - chemistry , total synthesis , sequence (biology) , quinone , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry
A mechanistically inspired tandom Dess–Martin periodinane (DMP) induced oxidation sequence converts anilides into N ‐substituted p ‐quinones or o ‐azaquinones depending on the aromatic nucleus substitution. The application of this technology resulted in an expedient total synthesis of the potent anti‐arthritic agent epoxyquinomycin B (see picture).