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Synlett 1997; 1997(2): 159-160
DOI: 10.1055/s-1997-751
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An Enantioselective Synthesis of (-)-Nonactic Acid and (+)-8-epi-Nonactic Acid Using Microbial Reduction

Kazuhiko Takatori, Kenji Tanaka, Katsunori Matsuoka, Kazuyoshi Morishita, Masahiro Kajiwara*
  • *Department of Medicinal Chemistry, Meiji College of Pharmacy 1-22-1 Yato-cho, Tanashi-shi, Tokyo 188, JAPAN
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Publication Date:
31 December 2000 (online)

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An enantioselective synthesis of (-)-nonactic acid (2a) and (+)-8-epi-nonactic acid (2b) is described. The microbial reduction of the dl-ketone 3 with baker's yeast gave two easily separable diastereomeric alcohols 11a and 11b, each in over 97% ee. These alcohols were converted to 2a and 2b in 4 steps.

nonactic acid - nonactin - microbial reduction - enantioselective reduction - iodo-etherification