Enantioselective synthesis of the 6,8-dioxabicyclo-[3.2.1]octane skeleton by asymmetric dihydroxylation
作者:Joseph A. Turpin、Leland O. Weigel
DOI:10.1016/s0040-4039(00)60985-1
日期:1992.10
Sharpless asymmetric dihydroxylation (AD) of 6-hepten-2-one with AD-mix-alpha(R) 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.