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Synlett 2001; 2001(5): 0694-0696
DOI: 10.1055/s-2001-13382
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Total Synthesis of Stevastelin B, a Novel Immunosuppressant

Naoki Kohyama* , Yukio Yamamoto
  • *Graduate School of Human and Environmental Studies, Kyoto University, Sakyo-ku, Yoshida, Kyoto 606-8501, Japan; Fax + 81-75-753-2999; E-mail: yuyamamo@ip.media.kyoto-u.ac.jp
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Publication Date:
31 December 2001 (online)

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Total synthesis of stevastelin B is described. Evans asymmetric aldol methodology and Roush asymmetric allylation were used to construct four consecutive stereo-centers on the octadecanoic acid moiety of stevastelin B. Subsequent coupling with a dipeptide and macrolactamization gave stevastelin B. The flexibility of this route could allow the synthesis of many analogues for biological tests, which cannot be obtained from natural sources.

total synthesis - stevastelin B - immunosuppressant - asymmetric aldol reaction - asymmetric allylation