C -Nucleosides and Related Compounds. IV. The Synthesis and Chemistry of D,L-2,5-Anhydroallose Derivatives

Abstract

Methyl β-nitroacrylate (1) reacted with furan to give the corresponding Diels–Alder adduct, which was converted to D,L-3,4-di-O-isopropylidene-2,5-anhydroallose (9) in a five-step sequence in 14% yield, based on 1. The conversion of 9 to its oxime, semicarbazone, and thiosemi-carbazone is described, as well as the synthesis of the free aldehyde 15, and of the Wittig reaction product 14.