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The Reductive Fragmentation of 7‐Hydroxy‐9,10‐dioxotaxoids
Author(s) -
Appendino Giovanni,
covich Alain,
Bettoni Piergiorgio,
Dambruoso Paolo,
Sterner Olov,
Fontana Gabriele,
Bombardelli Ezio
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300376
Subject(s) - chemistry , aldol reaction , fragmentation (computing) , cerium , combinatorial chemistry , stereochemistry , organic chemistry , medicinal chemistry , catalysis , computer science , operating system
The retro‐aldol reductive fragmentation of different structural types of 7‐hydroxy‐9,10‐dioxotaxoids was investigated, showing that the reaction is typical of taxanes and requires cerium( III ) promotion with NaBH 4 in protic medium and alkylboron (aluminium) hydrides in aprotic solvents. The resulting 7,8‐ seco ‐taxanes are key intermediates for the synthesis of a novel class of anticancer taxanes endowed with a unique pattern of in vivo biological activity. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)