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Synlett 1998; 1998(1): 79-80
DOI: 10.1055/s-1998-1577
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Synthesis of a Bicyclic Cation Related to Sterol Biosynthesis and Its Chemical Destiny, Part II

Mugio Nishizawa* , Hiroko Takao, Yoshihiro Iwamoto, Hidetoshi Yamada, Hiroshi Imagawa
  • *Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8055, Japan; E-mail: mugi@mb.infoeddy.ne.jp
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Publication History

Publication Date:
31 December 2000 (online)

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A 9α-substituted bicyclic tert-alcohol 3 has been selectively prepared by the Hg(OTf)2-induced olefin cyclization of tert-butyl (Z,E)-bishomofarnesate. Bicyclic cation 4, which is related to the sterol biosynthesis, was generated by the reaction of 3 with BF3. Although the cation 4 can take boat form conformation through flipping, cyclization took place to give 6/6/5 fused compound 5 as the sole tricyclic product via chair/chair cation.

sterol biosynthesis - 6/6/5 fused tricyclic products - mercuric triflate - biomimetic olefin cyclization