U.S. patents available from 1976 to present.
U.S. patent applications available from 2005 to present.

Stereoselective preparation of hexahydro dibenzopyranones and intermediates therefor

Patent 4102902 Issued on July 25, 1978. Estimated Expiration Date: Icon_subject November 10, 1996. Estimated Expiration Date is calculated based on simple USPTO term provisions. It does not account for terminal disclaimers, term adjustments, failure to pay maintenance fees, or other factors which might affect the term of a patent.

Patent References

3856820

3856821

3856822

Inventors

Assignee

Application

No. 05/740502 filed on 11/10/1976

US Classes:

549/391, Plural chalcogens bonded directly to the tricyclo ring system560/256, Polycyclo-alicyclic ring system in alcohol moiety568/327, Bicyclo ring system568/329Alicyclic ring containing

Examiners

Primary: Chan, Nicky

Attorney, Agent or Firm

International Classes

C07D 311/00 (20060101)
C07D 311/80 (20060101)

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 ଲ-pinenes.

Other References

  • Mechoulam et al., J. Amer. Chem. Soc., 89, 4552 (1967)
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