Synlett 1997; 1997(1): 121-122
DOI: 10.1055/s-1997-714
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
22 March 2004 (online)

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.