A Convenient Stereoselective Synthesis of (1R,2S,3R,4S)-3-(Neopentyloxy)isoborneol |
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Authors: | Xavier Verdaguer,Iolanda Marchueta,Jordi Tormo,Albert Moyano,Miquel A. Peric s,Antoni Riera |
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Affiliation: | Xavier Verdaguer,Iolanda Marchueta,Jordi Tormo,Albert Moyano,Miquel A. Pericàs,Antoni Riera |
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Abstract: | A convenient preparation of (1R,2S,3R,4S)-3-(neopentyloxy)isoborneol (= (1R,2S,3R,4S)-3-(2,2-dimethyl-propoxy)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol; 1a ), a valuable chiral auxiliary, is described. The synthesis involves six steps starting from the readily available camphorquinone ( 5 ) and gives 1a in 48% overall yield. The key step is the chemoselective hydrolysis of the less hindered 1,3-dioxolane moiety in the camphorquinone di-acetal 4 . |
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