APPLICATION OF SUGAR ALLYLTIN DERIVATIVES FOR THE PREPARATION OF HETEROCYCLIC COMPOUNDS

摘要

Controlled fragmentation of sugar allyltin, derivative of D-glucose, provided the eight carbon atom synthon: (2R,3S,4R)-tris(benzyloxy)oct-5,7-diene, which was used for the preparation of complex heterocyclic compounds. First step involved formation of the corresponding oxime, which underwent-under high pressure-the oxime/olefin cyclization (the alternative Diels-Alder product was not formed). Proper functionalization of the latter led to the tricyclic product.