Enantioselective synthesis of the 6,8-dioxabicyclo-[3.2.1]octane skeleton by asymmetric dihydroxylation

Article abstract of DOI:10.1016/S0040-4039(00)60985-1

Sharpless asymmetric dihydroxylation (AD) of 6-hepten-2-one with AD-mix-α followed by acidification gives (1S,5R)-5-methyl-6,8-dioxabicyclo[3.2.1]octane in moderate ee. This methodology defines a two-pot enantioselective construction of the (-)-frontalin and brevicomin skeleton from the corresponding 2-alkyl-1,3-dithiane and 5-bromo-1-hexene derivatives.