241815-02-1Relevant articles and documents
A synthesis of taxanes by lactam-sulfoxide ring contraction and intramolecular pinacol coupling
Takatori, Kazuhiko,Takeuchi, Yoshinari,Shinohara, Yuka,Yamaguchi, Kenji,Nakamura, Masayuki,Hirosawa, Tatsuya,Shimizu, Takeshi,Saito, Masae,Aizawa, Shouich,Sugiyama, Osamu,Ohtsuka, Yasuo,Kajiwara, Masahiro
, p. 975 - 977 (1999)
A synthesis of the taxane ring system is described. The A-ring moiety 5, containing the carbons for construction of the Bring, was prepared from Wieland-Miescher ketone via Beckmann fragmentation of the oxime 10. The B- ring was formed by means of 12-membered lactam-sulfoxide ring contraction. The formation of the C-ring was carried out by aldol condensation of the resulting AB-ring moiety 3 followed by intramolecular pinacol coupling to give the tricyclic diol 23.