31207-73-5Relevant articles and documents
Synthesis of Ambrox from labdanolic acid
Castro, Juan M,Salido, Sofía,Altarejos, Joaquín,Nogueras, Manuel,Sánchez, Adolfo
, p. 5941 - 5949 (2002)
A synthesis of the valuable amber-type odorant Ambrox from labdanolic acid (main diterpenoid of the acid fraction of non-polar extracts of Cistus ladaniferus L.) is reported. The conversion is based on (a) the α,β-dehydrogenation of methyl labdanolate using an organoselenium reagent, (b) subsequent oxidative degradations of the side chain, and (c) final acid-promoted cyclization of the resulting tetranorlabdan-8α,12-diol. The influence of the temperature and solvent in the cyclization of the diol with p-toluenesulfonic acid is also described. Thus, Ambrox has been obtained by a six-step procedure in 33% overall yield from methyl labdanolate.