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Synthesis of Enantiomerically Pure Morphan Analogues from α‐ D ‐Glucose
Author(s) -
Streicher Benedikt,
Wünsch Bernhard
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200101)2001:1<115::aid-ejoc115>3.0.co;2-f
Subject(s) - chemistry , acetal , acylation , intramolecular force , yield (engineering) , stereochemistry , organic chemistry , catalysis , materials science , metallurgy
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 .