A series of 1, 2-bis-methylenecycloalkane monoepoxides (2a-e) was prepared from the related 12-to 16-membered cyclic ketones. Reduction with lithium in ammonia afforded the corresponding trans-and cis-2-methylcycloalkenylmethanols (3a/4a-3e/4e) in ratios of 92: 8- 78: 22. Sharpless epoxidation of these allylic alcohols with 0.6 equivalents of the reagent prepared from titanium isopropoxlde,(+)-diisopropyl tartrate, and t-butylhydroperoxide ...
