A CONVENIENT STEREOSELECTIVE SYNTHESIS OF (1R,2S,3R,4S)-3-(NEOPENTYLOXY)ISOBORNEOL

Citation
X. Verdaguer et al., A CONVENIENT STEREOSELECTIVE SYNTHESIS OF (1R,2S,3R,4S)-3-(NEOPENTYLOXY)ISOBORNEOL, Helvetica Chimica Acta, 81(1), 1998, pp. 78-84
Citations number
36
Categorie Soggetti
Chemistry
Journal title
ISSN journal
0018019X
Volume
81
Issue
1
Year of publication
1998
Pages
78 - 84
Database
ISI
SICI code
0018-019X(1998)81:1<78:ACSSO(>2.0.ZU;2-5
Abstract
A convenient preparation of(1 R,2S,3R,4S)-3-(neopentyloxy)isoborneol , 2-dimethylpropoxy)-1,7,7-trimethylbicyclo[2.2.1]; heptan-2-ol; 1a). a valuable chiral auxiliary, is described. The synthesis involves six st eps starting from the readily available camphorquinone (5) and gives 1 a in 48 % overall yield. The key Step is the chemoselective hydrolysis of the less hindered 1,3-dioxolane moiety in the camphorquinone di-ac etal 4.