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Syntheses of apogalanthamine analogs as α‐adrenergic blocking agents. IX . Syntheses of optically active 8‐hydroxy‐6‐methyl‐5,6,7,8‐tetrahydrodibenz[ c,e ]azocines
Author(s) -
Kihara Masaru,
Ohnishi Kuniyoshi,
Kobayashi Shigeru
Publication year - 1988
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570250123
Subject(s) - chemistry , ethanolamine , optically active , hydrolysis , stereochemistry , kinetic resolution , medicinal chemistry , organic chemistry , catalysis , enantioselective synthesis
(8 R ) and (8 S )‐Hydroxy‐6‐methyl‐5,6,7,8‐tetrahydrodibenz[ c,e ]azocines ( R ‐ and S ‐ 1 ) were synthesized by oxidative kinetic resolution of N ‐(2‐iodobenzyl)‐β‐(2‐iodophenyl)ethanolamine ( 8 ), followed by cyclization of the optically active acetates ( R ‐ and S ‐ 6 ) of R‐ and S ‐ 8 with zero‐valent nickel to (8 R )‐ and (8 S )‐acetoxyazocines ( R ‐ and S ‐ 7 ), and by hydrolysis of the acetates ( R ‐ and S ‐ 7 ).