Affiliation:
1. C.N.R., Istituto di Chimica del Riconoscimento Molecolare, Via L. Mancinelli 7, 20131 Milano, Italy
Abstract
The enantioselective preparation of the two diastereoisomeric forms of 2,15-dihydroxycalamele‘ne and 2-methoxycalamenene is here described. The (7 S,10 R) and (7 R,10 R) isomers of these natural products were synthesized starting from (5 R,8 S)-methyl-4-hydroxy-8-isopropyl-5-methyl-5,6,7,8-tetrahydronaphthalene-2-carboxylate and (5 R,8 R)-methyl-4-hydroxy-8-isopropyl-5-methyl-5,6,7,8-tetrahydronaphthalene-2-carboxylate, respectively, in turn preparable from (-)-menthone and (+)-isomenthone. The NMR analysis of the obtained sesquiterpenes allow assigning (7 R,10 S) absolute configuration to the natural occurring 2,15-dihydroxycalamelene.
Subject
Complementary and alternative medicine,Plant Science,Drug Discovery,Pharmacology,General Medicine