Tetrahedron letters

A new route for the construction of the AB-ring core of Taxol

…, K Tsutsumi, T Morimoto, H Kurosawa, K Kakiuchi

Index: Shimada, Yumi; Nakamura, Makoto; Suzuka, Toshimasa; Matsui, Junji; Tatsumi, Ryo; Tsutsumi, Ken; Morimoto, Tsumoru; Kurosawa, Hideo; Kakiuchi, Kiyomi Tetrahedron Letters, 2003 , vol. 44, # 7 p. 1401 - 1403

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Citation Number: 19

Abstract

A new method for the construction of the AB-ring core of Taxol was developed utilizing a new skeletal transformation protocol as a pivotal step. The acid-catalyzed rearrangement of the cyclopentenone–allene photoadduct gave a bridged seven-membered ketone, which was easily transformed, using the intramolecular Suzuki reaction and the oxidative cleavage of the vicinal diol, to the bicyclic diketone.