Synlett 2013; 24(12): 1545-1548
DOI: 10.1055/s-0033-1338961
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (S,5Z,8E,10E)-12-Hydroxyheptadeca-5,8,10-trienoic Acid (12S-HHT) and its Analogues

Authors

  • Toshifumi Tojo

    a   Department of Bioengineering, Tokyo Institute of Technology, Box B52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan   Fax: +81(45)9245789   Email: ykobayas@bio.titech.ac.jp
  • Qian Wang

    a   Department of Bioengineering, Tokyo Institute of Technology, Box B52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan   Fax: +81(45)9245789   Email: ykobayas@bio.titech.ac.jp
  • Toshiaki Okuno

    b   Department of Biochemistry, Juntendo University School of Medicine, Hongo 2-1-1, Bunkyo-ku, Tokyo 113-8421, Japan
  • Takehiko Yokomizo

    b   Department of Biochemistry, Juntendo University School of Medicine, Hongo 2-1-1, Bunkyo-ku, Tokyo 113-8421, Japan
  • Yuichi Kobayashi*

    a   Department of Bioengineering, Tokyo Institute of Technology, Box B52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan   Fax: +81(45)9245789   Email: ykobayas@bio.titech.ac.jp
Further Information

Publication History

Received: 09 April 2013

Accepted after revision: 10 May 2013

Publication Date:
14 June 2013 (online)


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Abstract

Natural 12S-HHT and its analogues were synthesized for study of structure and activity relationship toward the BLT2 receptor. The Suzuki–Miyaura coupling was used for construction of the 8E,10E-diene moiety of 12S-HHT and analogues of (12R)- and 12-keto-types, whereas Wittig reaction was used for the synthesis of (8Z)- and (8Z,12R)-isomers.