The enantioselective preparation of the two diastereoisomeric forms of 2,15-dihydroxycalamelene and 2-methoxycalamenene is here described. The (7S,10R) and (7R,10R) isomers of these natural products were synthesized starting from (5R,8S)-methyl-4-hydroxy-8-isopropyl-5-methyl-5,6;7,8-tetrahydronaphthalene-2-carboxylate and (5R,8R)-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 (7R,10S) absolute configuration to the natural occurring 2,15-dihydroxycalamelene.
Stereoselective Synthesis of 2,15-Dihydroxycalamenene and 2-Methoxycalamenene. Determination of the Configuration of Natural 2,15-Dihydroxycalamenene
Serra;Stefano
2015
Abstract
The enantioselective preparation of the two diastereoisomeric forms of 2,15-dihydroxycalamelene and 2-methoxycalamenene is here described. The (7S,10R) and (7R,10R) isomers of these natural products were synthesized starting from (5R,8S)-methyl-4-hydroxy-8-isopropyl-5-methyl-5,6;7,8-tetrahydronaphthalene-2-carboxylate and (5R,8R)-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 (7R,10S) absolute configuration to the natural occurring 2,15-dihydroxycalamelene.File in questo prodotto:
Non ci sono file associati a questo prodotto.
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
