A new route for the construction of the AB-ring core of Taxol |
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| Authors: | Yumi ShimadaMakoto Nakamura Toshimasa SuzukaJunji Matsui Ryo TatsumiKen Tsutsumi Tsumoru MorimotoHideo Kurosawa Kiyomi Kakiuchi |
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| Institution: | a Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara 630-0101, Japan
b Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan |
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| 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. |
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