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Synlett 1995; 1995(6): 650-652
DOI: 10.1055/s-1995-5033
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Synthesis of Dicarboxylic Monoesters with Cyclic Anhydrides under High Pressure

Takeshi Shimizu* , Ryoichi Kobayashi, Hiromichi Ohmori, Tadashi Nakata1
  • *The Institute of Physical and Chemical Research (RIKEN), Wako-shi, Saitama 351-01, Japan, Fax +81 48 462 4666
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Publication Date:
31 December 2000 (online)

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The reaction of sterically hindered alcohols with cyclic anhydrides in pyridine in the presence of N,N-dimethylaminopyridine (DMAP) under high pressure directly afforded the dicarboxylic monoesters in high yields. The present method was successfully applied to the synthesis of the 2’,7-dihemiesters of taxol as water-soluble prodrugs.

Dicarboxylic monoester - Cyclic anhydride - Hindered alcohol - High pressure - Taxol