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The First Model of the Neocarzinostatin Chromophore with an Epoxide Ring and a Carbonate Moiety
Author(s) -
Eckhardt Matthias,
Brückner Reinhard
Publication year - 1996
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199610931
Subject(s) - moiety , ring (chemistry) , epoxide , pharmacophore , substrate (aquarium) , reagent , chemistry , stereochemistry , neocarzinostatin , chromophore , combinatorial chemistry , organic chemistry , catalysis , dna , biochemistry , oceanography , geology
A seven‐step synthesis starting from 1 furnished the dienediyne analog 2 of the pharmacophore 3 of the antitumor agent neocarzinostatin. The eleven‐membered ring of 2 was formed by the McMurry cyclization of a ketoaldehyde precursor. The resulting C = C bond was epoxidized selectively by taking advantage of a combination of substrate and reagent control. Tf = CF 3 SO 2 , Ar = aryl.