An Enantioselective Synthesis of Beta-Eudesmol.
Abstract
Beta-Eudesmol is a bicyclic sesquiterpene which is commonly found in nature. It has been a synthetic target for many researchers, most of whom used approaches based on a Robinson ring annulation reaction to generate the required decalone nucleus with a 4a-methyl substituent. Their syntheses are all of racemic Beta-eudesmol. An enantioselective synthesis of (+)-Beta-eudesmol using diastereoselective cyclopropanation to install the 4a-methyl group in the natural configuration has been developed. The method involves cyclopropanation of a chiral ene ketal so that one face of the double bond reacts preferentially. By this route (+)-Beta-eudesmol was prepared in 7% yield over 12 steps as a 7 to 1 ratio of enantiomers
Document Details
- Document Type
- Technical Report
- Publication Date
- Jan 01, 1986
- Accession Number
- ADA176547
Entities
People
- James A. Fryling
Organizations
- Air Force Institute of Technology