SYNTHESIS AND CONFORMATIONAL-ANALYSIS OF 2,9-DISUBSTITUTED 1-OXAQUINOLIZIDINES

Authors
BORJESSON L CSOREGH I WELCH CJ
Citation
L. Borjesson et al., SYNTHESIS AND CONFORMATIONAL-ANALYSIS OF 2,9-DISUBSTITUTED 1-OXAQUINOLIZIDINES, Journal of organic chemistry, 60(10), 1995, pp. 2989-2999
Citations number
50
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
60
Issue
10
Year of publication
1995
Pages
2989 - 2999
Database
ISI
SICI code
0022-3263(1995)60:10<2989:SACO21>2.0.ZU;2-G
Abstract
The synthesis of l)oxy)pentyl)-2-(hydroxymethyl)-1-oxaquinolizidine (2 9a) from (S)-malic acid, 1,5-pentanediol, and trifluoroacetamide is re ported. Conformational analysis using molecular mechanics calculations and NMR spectroscopy of 29 together with X-ray crystallographic analy sis of (2S,10S)-2-(hydroxymethyl)-1-oxaquinolizidine (30) are used to determine the structure and conformational preferences of these 1-oxaq uinolizidine derivatives.