Stereoselective preparation of hexahydro dibenzopyranones...

C - Chemistry – Metallurgy – 07 – D

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260/359.9

C07D 311/80 (2006.01)

Patent

CA 1101875

Abstract of the Disclosure This invention provides a process comprising the reaction of an optically active 4-(4-substituted-2,6- dihydroxyphenyl)-6,6-dimethyl-2-norpinanone with an acid to provide an optical isomer of a 1-hydroxy-3-substituted-6,6- dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9- one, wherein the hydrogen atoms at the 6a and 10a positions may be in either the Cis or trans conformation. The optically active norpinanones are prepared by reaction of a 5-sub- stituted resorcinol with an optically active 6,6-dimethyl- 2,4-diacetoxy-2-norpinene or an optically active 6,6-di- methyl-2,2-diacetoxy-9-norpinene, which compounds are derived from known optically active .beta.-pinenes.

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