Stereoselective preparation of hexahydro dibenzopyranones and in

Details Stereoselective preparation of hexahydro dibenzopyranones and in Stereoselective preparation of hexahydro dibenzopyranones and in

1979-04-17

1980-06-17

Morgenstern, Norman

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

Organic compounds

Oxygen containing

C07C 4982

Patent

active

042083516

ABSTRACT:
An optically active 4-(4-substituted-2,6-dihydroxyphenyl)-6,6-dimethyl-2-norpinanone is reacted with a protonic acid to provide an optical isomer of a cis-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibe nzo[b,d]pyran-9-one. Reaction of said norpinanone with a Lewis acid provides an optical isomer of trans-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-di benzo[b,d]pyran-9-one. The optically active norpinanones are prepared by reaction of a 5-substituted-resorcinol with an optically active 6,6-dimethyl-2,4-diacetoxy-2-norpinene or an optically active 6,6-dimethyl-2,2-diacetoxy-3-norpinene, which compounds are derived from optically active .beta.-pinenes.

REFERENCES:
patent: 2834814 (1958-05-01), Bain et al.
patent: 4061686 (1977-12-01), Hall et al.

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