Process for producing L-ambrox

Details Process for producing L-ambrox Process for producing L-ambrox

1992-12-23

1994-03-01

Dentz, Bernard

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

562501, 562497, 549299, C07C 53136, C07D30792

Patent

active

052909557

ABSTRACT:
(-)-2,5,5,8a-Tetramethyl-1-(carboxymethyl)-2-hydroxydecalin is subjected to lactonization by dehydration to form decahydro-3a,6,6,9a-tetramethyl(3a.alpha.,5a.beta.,9a.alpha.,9b.beta.)-(+) -naphtho[2,1-b]furan-2(1H)-one, which is then reduced with a metal hydride to convert it into (-)-2,5,5,8a-tetramethyl-1-(carboxymethyl)-2-hydroxydecalin, followed by dehydrative cyclization to give L-ambrox.
The (-)-2,5,5,8a-tetramethyl-1-(carboxymethyl)-2-hydroxydecalin is produced from its racemic mixture. The resolution is performed using a 1-(aryl)ethylamine. The starting material for the synthesis is beta-ionone.

REFERENCES:
patent: 3050532 (1962-08-01), Schumacher et al.
Chemical Abstracts, vol. 94, No. 3, AN 94: 15913q, Jan. 19, 1981.
Saito et al., Chemistry Letters, pp. 729-732 (1983).

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