14β-Hydroxybaccatin III, a compound with limited availability by natural sources, is the starting material for the synthesis of the second-generation anticancer taxoid ortataxel. The 7-tert-butoxycarbonyl (1a) and 7-triethylsilyl (1b) derivatives of 14β-hydroxybaccatin III 1,14-carbonate were synthesized from 10-deacetylbaccatin III (3). The crucial steps were (a) the C14β hydroxylation of the corresponding 13-oxobaccatin III derivatives by oxaziridine-mediated electrophilic oxidation and (b) the reduction of the C13 carbonyl group with sodium or alkylammonium borohydrides. This protocol provides a practical way for the semisynthesis of ortataxel from 10-deacetylbaccatin III, a compound readily available from various yews.
Diastereoselective 14β-Hydroxylation of Baccatin III Derivatives / E. Baldelli, A. Battaglia, E. Bombardelli, G. Carenzi, G. Fontana, A. Gambini, M.L. Gelmi, A. Guerrini, D. Pocar. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 68:25(2003), pp. 9773-9779.
Titolo: | Diastereoselective 14β-Hydroxylation of Baccatin III Derivatives |
Autori: | |
Settore Scientifico Disciplinare: | Settore CHIM/06 - Chimica Organica |
Data di pubblicazione: | 2003 |
Rivista: | |
Tipologia: | Article (author) |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1021/jo0347112 |
Appare nelle tipologie: | 01 - Articolo su periodico |