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
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.