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Enediyne Compounds Equipped with Acid‐, Base‐ and Photo‐Sensitive Triggering Devices. Chemical Simulation of the Dynemicin A Reaction Cascade
Author(s) -
Nicolaou K. C.,
Dai W.M.,
Wendeborn S. V.,
Smith A. L.,
Torisawa Y.,
Maligres P.,
Hwang C.K.
Publication year - 1991
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.199110321
Subject(s) - enediyne , nucleophile , cascade , chemistry , combinatorial chemistry , base (topology) , stereochemistry , photochemistry , computational chemistry , organic chemistry , chromatography , mathematical analysis , mathematics , catalysis
Even under very mild basic conditions , the NH compound 2 is generated from the enediyne 1 . Compound 2 proved too labile to be isolated, but could be trapped with nucleophiles such as PhOH and PhSH, resulting in the formation of the dibenzo compounds 4 (via 3 ), among other products. Compounds 2 —like several other newly synthesized compounds—exhibits DNA‐cleaving activity.