Synthesis of 1-homoaustraline

Abstract

The 1,3-dipolar cycloaddition of a five-membered cyclic nitrone derived from malic acid and unsaturated d-threo-hexonolactone leads to a single adduct, which was transformed into 1-homoaustraline via a reaction sequence involving rearrangement of the six-membered lactone ring into the five-membered one, removal of the terminal carbon atom from the sugar chain, reduction of the lactone fragment into triol, protection of primary hydroxy groups, mesylation of the secondary one, cleavage of the N–O bond, and the intramolecular alkylation of the nitrogen atom.