A synthesis of taxanes by lactam-sulfoxide ring contraction and intramolecular pinacol coupling

Authors
Takatori, K Takeuchi, Y Shinohara, Y Yamaguchi, K Nakamura, M Hirosawa, T Shimizu, T Saito, M Aizawa, S Sugiyama, O Ohtsuka, Y Kajiwara, M
Citation
K. Takatori et al., A synthesis of taxanes by lactam-sulfoxide ring contraction and intramolecular pinacol coupling, SYNLETT, 1999, pp. 975-977
Citations number
19
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Year of publication
1999
Pages
975 - 977
Database
ISI
SICI code
0936-5214(1999):<975:ASOTBL>2.0.ZU;2-P
Abstract
A synthesis of the taxane ring system is described. The A-ring moiety 5, co ntaining the carbons for construction of the Bring, was prepared from Wiela nd-Miescher ketone via Beckmann fragmentation of the oxime 10. The B-ring w as formed by means of 12-membered lactam-sulfoxide ring contraction. The fo rmation of the C-ring was carried out by aldol condensation of the resultin g AB-ring moiety 3 followed by intramolecular pinacol coupling to give the tricyclic diol 23.