High-pressure mediated Diels-Alder reaction of di-l-menthyl acetoxy-methylenemalonate with furan: Enantioselective synthesis of β-D-ribofuranosylmalonate, a prospective synthon for C-nucleoside

Abstract

β-D-Ribofuranosylmalonate [D]- 4 has been synthesized through high-pressure Diels-Alder reaction of furan with di-l-menthyl acetoxymethylenemalonate ( 1b), followed by reductive retrograde aldol CC bond fission. A mechanism accounting for the observed diastereoselectivity in the Diels-Alder reaction is proposed.