Chiral tetrahydrofuran synthesis from D-ribose diphenyl dithioacetal

摘要

Treatment of D-ribose diphenyl dithioacetal 1 with 4.2 equivalents of #pi#-CPBA results in formation of teh bis(phenylsulfone)4, which is likely the result of an oxidation-elimination-cyclization sequence. Tetrahydrofuran 4 is protected as the isopropylidene derivative 5. The latter is alkylated to generate 6, and 5 undergoes reductive elimination to the olefin 7.