
%0 Journal Article
%A Rickards, RW 
%A Watson, WP 
%T Conversion of (+)-(R)-Limonene into (+)-(1S,4R)-p-mentha-2,8-dien-1-ol, an intermediate in the synthesis of tetrahydrocannabinoids
%J Australian Journal of Chemistry
%D 1980/02/01
%V 33
%N 2
%P 451-454
%K 
%R https://doi.org/10.1071/CH9800451
%U https://www.publish.csiro.au/paper/CH9800451 
%X (+)-(1S,4R)-p-Mentha-2,8-dien-1-ol (3), an important intermediate in the synthesis of (-)-&#916;9-trans-6a,10a-tetrahydrocannabinol (1) and other tetrahydrocannabinoids, is conveniently prepared from (+)-(R)-limonene (5) by rearrangement of its (1S,2R)-1,2-epoxide (7). Similar rearrangement of the diastereoisomeric (1R,2S)-1,2-epoxide (6) yields (+)-(2S,4R)-p-mentha-1(7),8-dien-2-ol (12), a major constituent of gingergrass oil. 
