Abstract
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.
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