Stereoselective preparation of hexahydro dibenzopyranones and in

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

1976-11-10

1978-07-25

Chan, Nicky

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260590C, 560256, C07D31180

Patent

active

041029020

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: 3856820 (1974-12-01), Loev
patent: 3856821 (1974-12-01), Loev
patent: 3856822 (1974-12-01), Bender et al.
Mechoulam et al., J. Amer. Chem. Soc., 89, 4552 (1967).

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