Facile Construction of the Tricyclo[5.2.1.01,5]decane Ring System by Intramolecular Double Michael Reaction:  Highly Stereocontrolled Total Synthesis of (±)-8,14-Cedranediol and (±)-8,14-Cedranoxide

Masataka Ihara,* Kei Makita, and Kiyosei Takasu
Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan
J. Org. Chem., 1999, 64 (4), pp 1259–1264
DOI: 10.1021/jo981996n
Publication Date (Web): January 28, 1999
Copyright © 1999 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

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It was observed that the synthesis of tricyclo[5.2.1.01,5]decane 10 can be performed effectively by the intramolecular double Michael reaction of 5-(5-methoxycarbonyl-4-pentenyl)-2-cyclopenten-1-one (9). Highly stereocontrolled total syntheses of (±)-8,14-cedranediol (2) and (±)-8,14-cedranoxide (1) were accomplished by the application of this methodology. Heating 5-(1,5-dimethyl-5-ethoxycarbonylpent-4-enyl)-2-cyclopenten-1-one (15) with TMSCl, Et3N, and ZnCl2 in o-dichlorobenzene at 150 °C provided (±)-(1R*,2R*,5R*,6R*,7S*)-2,6-dimethyl-6-ethoxycarbonyltricyclo[5.2.1.01,5]-decan-9-one (16) as a single isomer. The product 16 was stereoselectively converted into the above cedranoids 2 and 1 through ring expansion chemistry.

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History

  • Published In Issue February 19, 1999
  • Received October 2, 1998

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