An efficient, enantioselective preparation of (R)-muscone employing a diastereoselective Simmons-Smith cyclopropanation is described. Cyclopropanation is directed via chelation control by a homochiral ketal protecting group derived from unnatural tartaric acid. The overall yield of (R)-muscone (>95% R) from commercially available cyclopentadecanone is 60% over seven steps.
ASJC Scopus subject areas
- Organic Chemistry