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Synlett 1999; 1999(S1): 975-977
DOI: 10.1055/s-1999-3101
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A Synthesis of Taxanes by Lactam-sulfoxide Ring Contraction and Intramolecular Pinacol Coupling

Kazuhiko Takatori* , Yoshinari Takeuchi, Yuka Shinohara, Kenji Yamaguchi, Masayuki Nakamura, Tatsuya Hirosawa, Takeshi Shimizu, Masae Saito, Shouich Aizawa, Osamu Sugiyama, Yasuo Ohtsuka, Masahiro Kajiwara
  • *Department of Medicinal Chemistry, Meiji Pharmaceutical University, 2-252-1 Noshio, Kiyose-shi, Tokyo 204-8588, Japan; Fax +81(4 24)95 74 58; E-mail: kajiwara@my-pharm.ac.jp
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Publication Date:
31 December 1999 (online)

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A synthesis of the taxane ring system is described. The A-ring moiety 5, containing the carbons for construction of the B-ring, 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.

taxane - ring contraction - SmI2 - pinacol coupling - Beckmann fragmentation

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