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Synlett 1997; 1997(1): 121-122
DOI: 10.1055/s-1997-714
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Stereochemistry of a Unique Tricarbocyclic Compound Prepared by Superacid-Catalyzed Cyclization

Hisahide Tanimoto1 , Hiromasa Kiyota2 , Takayuki Oritani3 , Keita Matsumoto4
  • 1Department of Applied Biological Chemistry, Faculty of Agriculture, Tohoku University, 1-1 Tsutsumidori-Amamiyamachi, Aoba-ku, Sendai 981, Japan
  • 2Department of Applied Biological Chemistry, Faculty of Agriculture, Tohoku University, 1-1 Tsutsumidori-Amamiyamachi, Aoba-ku, Sendai 981, Japan, E-mail: kiyota@biochem.tohoku.ac.jp; Fax +81-22-717-8783
  • 3Department of Applied Biological Chemistry, Faculty of Agriculture, Tohoku University, 1-1 Tsutsumidori-Amamiyamachi, Aoba-ku, Sendai 981, Japan, Fax +81-22-717-8783
  • 4Research Center, Taisho Pharmaceutical Co., Ltd., 1-403 Yoshino-cho, Omiya 330 Japan
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Publication History

Publication Date:
22 March 2004 (online)

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Chlorosulfonic acid catalyzed cyclization reaction of β-monocyclonerolidol and β-monocyclofarnesol and corresponding acetates gave a unique rearranged product (2 S*, 3S*, 4aR*, 8aS*)-1,3,4,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-2H-2,4a-methanonaphthalen-3-ol, the structure of which was elucidated by X-ray analysis.

chlorosulfonic acid - unique tricarbocyclic compound - stereochemistry