An enantioselective preparation of (+)-β-eudesmol employing a diastereoselective Simmons-Smith cyclopropanation is described. Cyclopropanation of a bicyclic enone precursor is directed by use of the corresponding (2S,3S)-2,3-butanediol ketal. The overall yield of (+)-β-eudesmol (75% ee) from racemic 7-carbomethoxy-3,4,5,6,7,8-hexahydronaphthalen-l(2H)-one is 25% over eight steps.
ASJC Scopus subject areas
- Organic Chemistry