Hydroboration of terpenes—VIII

Add time:07/29/2019    Source:sciencedirect.com

d-(+)-Limonene can be converted into the corresponding bicyclic organoborinate intermediate, B-methoxy-4,8-dimethyl-2-borabicyclo[3.3.1]nonane, by cyclic hydroboration with borane in THF, followed by methanolysis, and distillation of the product. Alternatively, cyclic hydroboration of d-(+)-limonene with thexylborane provides the related bicyclic organoborane intermediate, B-thexyl-4,8-dimethyl-2-borabicyclo[3.3.1]nonane. Oxidation of the respective intermediates produces d-(−)-(1R, 2R, 4R)-limonene-2,9-diol. Protonation of the bicyclic thexyl intermediate, followed by oxidation, provides d-(−)-(1R, 2R, 4R)-carvomenthol. These results suggest that the cyclic hydroboration of dienes can provide a valuable means for controlling the exact site of hydroboration, leading to a stereoselective synthesis of alcohols.

We also recommend Trading Suppliers and Manufacturers of (1R,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2α-ol (cas 10334-13-1). Pls Click Website Link as below: cas 10334-13-1 suppliers

Prev:Synthesis of (−)-(1R,2R,4R,6S)-1,6-epoxy-4-benzyloxycyclohexan-2-ol, A key precursor to inositol monophosphatase inhibitors, from (−)-quinic acid
Next:Studien in der caranreihe—II)