31222-15-8Relevant articles and documents
PROCESS FOR THE PREPARATION OF OPTICALLY-ACTIVE COMPOUNDS
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Page/Page column 11-13, (2008/06/13)
A method of preparing enatiomerically enriched 3a,6,6,9a-tetramethyl-dodecahydro-naphtho[2,1-b]furan, formula (I), from (E,E)- homofarnesic acid or (E)-monocyclohomofarnesic acid by (a) reacting firstly with a chiral alcohol, (b) reacting the product of (a) with an acid to cause a first cyclisation, (c) producing an alcohol by reacting the product of (b) with a reducing agent and (d) causing a second cyclisation by reacting the product of (c) with an acid. The product of this process gives a mixture of both enantiomers with one in excess.
Total Synthesis of (-)-Ambrox from S-(+)-Carvone (part 6)
Verstegen-Haaksma, Anja A.,Swarts, Henk J.,Jansen, Ben J. M.,Groot, Aede de
, p. 10095 - 10106 (2007/10/02)
Conjugate addition of cyanide and allyl nucleophiles to S-(+)-carvone followed by annulation with methyl vinyl ketone gave the substituted decalones 2 and 3 stereoselectively.Both decalones were transformed into (-)-Ambrox via modification of the sidechain, methylation, conversion of the isopropenyl group and cyclization.