Download PDF
Synthesis 1988; 1988(1): 19-22
DOI: 10.1055/s-1988-27454
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Preparative Bioorganic Chemistry; 8.1 Efficient Enzymatic Preparation of (1R,4S)-(+)-4-Hydroxy-2-cyclopentenyl Acetate

Takeshi Sugai* , Kenji Mori
  • *Department of Agricultural Chemistry, The University of Tokyo, Yayoi 1-1-1, Bunkyo-ku, Tokyo 113, Japan
Further Information

Publication History

Publication Date:
12 September 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

An efficient method for the preparation of (1R,4S)-(+)- 4-hydroxy-2-cyclopentenyl acetate, a useful chiral starting material for the synthesis of prostaglandins, is described. A mixture of cis- and trans-3,5-diacetoxycyclopentene, readily obtainable on a preparative laboratory scale, was used as the substrate for the hydrolysis with commercially available pig pancreatic lipase (PPL). PPL hydrolyzed the substrate enantioselectively and substrate-selectively, yielding mainly the (+)-cis-monoacetate and trans-diacetate (Method A). The former was recrystallized to give the diastereomerically and optically pure (+)- cis-monoacetate. Ester exchange of cis/trans mixture of the diacetate in an organic solvent using enzymes as batch or flow system was also investigated (Method B). Method A was applicable to 0.25 mol of substrate, and yielded 0.127 mol (18 g, 51%) of optically pure (+)-monoacetate with recycling recovered materials.

      >