Synthesis of enantiomerically pure morphan analogues from alpha-D-glucose

The synthesis of the enantiomerically pure morphan analogue 19 starting with the methyl glucopyranoside 6 is described. Homologation, reduction, and acylation provide the heptopyranosamine derivatives 9a-c. After removal of the hydroxy group of 9c the intramolecular N/O-acetal formation of the Cbz-protected heptopyranosamine 18 succeeds to yield the morphan analog epoxyazocane 19.