Studies on the synthesis of chiral nonracemic 3,4-disubstituted azepanes, a formal synthesis of (+)- and (-)-balanol

Authors
Herdeis, C Mohareb, RM Neder, RB Schwabenlander, F Telser, J
Citation
C. Herdeis et al., Studies on the synthesis of chiral nonracemic 3,4-disubstituted azepanes, a formal synthesis of (+)- and (-)-balanol, TETRAHEDR-A, 10(23), 1999, pp. 4521-4537
Citations number
47
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
23
Year of publication
1999
Pages
4521 - 4537
Database
ISI
SICI code
0957-4166(199912)10:23<4521:SOTSOC>2.0.ZU;2-Z
Abstract
Sugar lactones were converted to 3,4-disubstituted azepanes and caprolactam derivatives by selective deoxygenation, functionalization and reductive cy clization. The cyclization proved troublesome with 6-azidolactols but led t o good results with the corresponding lactones. A formal synthesis of (+)- and (-)-balanol is reported. (C) 1999 Elsevier Science Ltd. All rights rese rved.