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Synthesis 1994; 1994(12): 1249-1254
DOI: 10.1055/s-1994-25674
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Synthesis of Compounds with Juvenile Hormone Activity; XXXI:1 Stereocontrolled Synthesis of (+)-Juvabione from a Chiral Sulfoxide

Hidenori Watanabe* , Hiroki Shimizu, Kenji Mori
  • *Department of Agricultural Chemistry, The University of Tokyo, Yayoi 1-1-1, Bunkyo-ku, Tokyo 113, Japan
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Publication Date:
25 April 2002 (online)

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A stereocontrolled synthesis of (+)-juvabione is described. The key step is a regioselective lithiation of a chiral (E)-butenyl sulfoxide 5 followed by stereoselective 1,4-addition to cyclohex-2-en-1-one. The chiral sulfoxide 5 was prepared by employing a microbial method.