151636-94-1Relevant articles and documents
Anomalous microbial transformations on the taxane ring of 10-DAB by a strain of the fungus Curvularia lunata: Transbenzoylation, transacetylation, and opening of the oxetane ring
Arnone, Alberto,Bava, Adriana,Fronza, Giovanni,Nasini, Gianluca
, p. 2000 - 2004 (2009)
The fermentation of 10-deacetylbaccatin III (10-DAB) (1) with Curvularia lunata afforded the taxane hemiacetals 2a and 3, characterized by extensive structural modification, including C-2 to C-1 transbenzoylation, oxidation of the C-2 hydroxyl, formation
PROCESSES FOR TAXANE DERIVATIVES AND INTERMEDIATES USEFUL THEREIN
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Page/Page column 31-32, (2008/06/13)
The application provides a process for the preparation of taxane derivatives and intermediates useful in such processes.
The Reductive Fragmentation of 7-Hydroxy-9,10-dioxotaxoids
Appendino, Giovanni,Noncovich, Alain,Bettoni, Piergiorgio,Dambruoso, Paolo,Sterner, Olov,Fontana, Gabriele,Bombardelli, Ezio
, p. 4422 - 4431 (2007/10/03)
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 NaBH4 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.
Synthesis of modified baccatins via an oxidation-reduction protocol
Appendino, Giovanni,Jakupovic, Jasmin,Cravotto, Giancarlo,Enriu, Renata,Varese, Marcella,Bombardelli, Ezio
, p. 3233 - 3236 (2007/10/02)
(12R)-7-trietylsilyl-11-dihydro-10-deacetylbaccatin III (2), -deacetylbaccatin III (4) and the 7,8-seco baccatin III (5a) were synthesized from 10-deacetylbaccatin III via an oxidation-reduction protocol.
THE CHEMISTRY AND OCCURRENCE OF TAXANE DERIVATIVES. XIII. THE OXIDATION OF 10-DEACETYLBACCATIN III
Appendino, Giovanni,Fenoglio, Ivana,Cravotto, Giancarlo,Varese, Marcella,Gariboldi, Pierluigi,Gabetta, Bruno
, p. 253 - 258 (2007/10/02)
The three secondary hydroxyls of 10-deacetylbaccatin III, 1, can be selectively oxidized.However, only the 13-dehydro derivative is stable under the reaction conditions, whereas the 10- and the 7-dehydro derivatives undergo epimerization at C-7 and oxetan