A NOVEL AND CHIRAL SYNTHESIS OF BOTH ENANTIOMERS OF TRANS-3-AMINO-4-HYDROXYHEXAHYDROAZEPINE, A KEY INTERMEDIATE FOR THE SYNTHESIS OF BALANOL

A NOVEL AND CHIRAL SYNTHESIS OF BOTH ENANTIOMERS OF TRANS-3-AMINO-4-HYDROXYHEXAHYDROAZEPINE, A KEY INTERMEDIATE FOR THE SYNTHESIS OF BALANOL

Both enantiomers of the hexahydroazepine (7), key intermediates for the synthesis of (-)-balanol (1) and its enantiomer, were effectively synthesized via the shortest route involving stannyl radical cyclization of the aldehyde (4) connected with oxime ether followed by the optical resolution of the...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1996/03/15, Vol.44(3), pp.624-626
Hauptverfasser: NAITO, Takeaki, TORIEDA, Mayumi, TAJIRI, Kazumi, NINOMIYA, Ichiya, KIGUCHI, Toshiko
Format: Artikel
Sprache:eng
Schlagworte:
3-amino-4-hydroxyhexahydroazepine
balanol
Chemistry
chiral synthesis
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
oxime ether
PKC inhibitor
Preparations and properties
radical cyclization
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Zusammenfassung:Both enantiomers of the hexahydroazepine (7), key intermediates for the synthesis of (-)-balanol (1) and its enantiomer, were effectively synthesized via the shortest route involving stannyl radical cyclization of the aldehyde (4) connected with oxime ether followed by the optical resolution of the resulting azepine (7).
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.44.624