Compounds and a novel process for their preparation

Details Compounds and a novel process for their preparation Compounds and a novel process for their preparation

2004-05-28

2008-09-02

Davis, Zinna N (Department: 1625)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ether doai

C514S716000, C568S583000, C568S626000, C568S700000, C568S704000, C568S715000

Reexamination Certificate

active

07420003

ABSTRACT:
The present invention is directed to a procedure for making an enantiomerically enriched compound containing a hydronaphthalene ring structure. The process involves reacting oxabenzonorbornadienes with nucleophiles using rhodium as a catalyst and in the presence of a phosphine ligand. The compounds synthesized may be used in pharmaceutical preparations for the treatment of a variety of diseases and conditions.

REFERENCES:
patent: 6569652 (2003-05-01), Eguchi et al.
Mirsadeghi et al, Journal of Organic Chemistry, vol. 50, pp. 4340-4345, 1985.
Derwent accession No. 1999-190628, Kyowa Hakko Kogyo KK: “Preparation of Optically Active Diol Compounds, e.g., Crixivan—Using Mircoorganism, e.g.,Rodococcus, Bacillus, Brevibacteriumor Gordona Species;” AU, A, 4031097, 19990304, DW199916.
Duan, et al., “Palladium-Catalyzed Reductive Couplings of Organic Halides with 7-Heteroatom Norbornadienes. New Synthetic Methods for Substituted Aryls andcis-1,2-Dihydro-1-Naphthyl Alcohols and Carbamates,”Organometallics 14:1608-1618 (1995).
Dubey, et al., “Synthesis of Dihydro Diols and Diol Epoxides of Benzo[ƒ]quinoline,”J. Org. Chem. 51:3407-3412 (1986).
Funk, et al., “Development of Chiral Stationary Phases for the Enantiomeric Resolution of Dihydrodiols of Polycyclic Aromatic Hydrocarbons by π-Donor-Acceptor Interactions,”J. Chromotography A. 659:57-68 (1994).
Hartwig, “Transition Metal Catalyzed Synthesis of Arylamines and Aryl Ethers from Aryl Halides and Triflates: Scope and Mechanism,”Angewandte Chemie Int. Ed. 37:2047-2067 (1998).
Kende, et al., “Novel Rearrangements during Dehydration of Nucleophile Adducts of Arene Oxides. A Reappraisal of Premercapturic Acid Structures,”J. Am. Chem. Soc. 97:4427-4428 (1975).
Lautens, et al., “Metal Catalyzed Hydrometalations and Their Applications in Synthesis,”Chemical Abstracts 129:244669 (1998).
Lautens, et al., “Scope of the Nickel Catalyzed Asymmetric Reductive Ring Opening Reaction. Synthesis of Enantiomerically Enriched Cyclohexenols,”Tetrahedron 54:1107-1116 (1998).
Lautens, et al., “Exploring the Reactivity of Dioxacyclic Compounds as a Route to Polysubstituted Decalins and Fused Polycycles,”J. Org. Chem. 63:647-656 (1998).
Lautens, et al., “Base-Induced Ring Opening of Aza- and Thiaoxa[3.2.1] and -[3.3.1]Bicycles as an Enantioselective Approach to Azepines, Thiepines, and Thiocines,”J. Org. Chem. 62:7080-7081 (1997).
Lautens, et al., “An Expedient Route for the Stereoselective Construction of Bridged Polyheterocyclic Ring Systems Using the Tandem ‘Pincer’ Diels-Alder Reaction,”J. Org. Chem. 62:4418-4427 (1997).
Moinet, et al., “Palladium-Catalyzed Asymmetic Hydrophenylation of 1,4-Dihydro-1,4-Epoxynaphthalene,”Tetrahedron Letters 36:2051-2052 (1995).
Posner, et al., “Organic Reactions at Alumina Surfaces. Mild and Selective Opening of Arene and Related Oxides by Weak Oxygen and Nitrogen Nucleophiles,”J. Am. Chem. Soc. 99:8214-8218 (1977).
Von Tugeln, et al., “Stereoselective Metabolism of 9-Methyl-, 9-Hydroxymethyl- and 9,10-Dimethylanthracenes: Absolute Configurations and Optical Purities ofTrans-Dihydrodiol Metabolites,”Carcinogenesis 7:1135-1141 (1986).
Widenhoefer, et al., “Direct Observation of C—O Reductive Elimination from Palladium Aryl Alkoxide Complexes to Form Aryl Ethers,”J. Am. Chem. Soc. 119:6787-6795 (1997).

Affiliated with

Also associated with

Rating

Compounds and a novel process for their preparation does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Compounds and a novel process for their preparation, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Compounds and a novel process for their preparation will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3969642