Stereoselective Synthesis of Methyl Epijasmonate

Abstract

Methyl epijasmonate (1) was stereoselectively synthesized from 3-hydroxymethylcyclopentanone (7). The intramolecular alkylation of bromoketone (8) or (9) was the key step to exclusively afford thermodynamically more stable oxahydrindanone (10) or (11). Synthesis was achieved in a 6% overall yield in 12 steps from (7).