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Synthesis of C‐2 Taxol Analogues
Author(s) -
Nicolaou Kyriacos Costa,
Couladouros Elias A.,
Nantermet Phillipe G.,
Renaud Joanne,
Guy Rodney Kiplin,
Wrasidlo Wolfgang
Publication year - 1994
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.199415811
Subject(s) - nucleophile , chemistry , ring (chemistry) , carbonyl group , molecule , stereochemistry , group (periodic table) , carbonate , nucleophilic addition , organic chemistry , catalysis
Nucleophilic ring opening of cyclic carbonates 1 leads regioselectively to the less substituted ester 2 . Moreover, for molecules with several carbonyl groups the reaction is chemoselective: In a taxol precursor the carbonate group and not one of the three additional carbonyl groups was attacked; the resulting esters were converted into taxol analogues that displayed differing cytotoxicities.