The First Model of the Neocarzinostatin Chromophore with an Epoxide Ring and a Carbonate Moiety | Zendy

Eckhardt Matthias | Zendy; Brückner Reinhard | Zendy

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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.

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