Synthesis of 7-membered carbocyclic compound having...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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Reexamination Certificate

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07094913

ABSTRACT:
The present invention relates to a synthesis of a 7-membered carbocyclic compound having diexomethylene groups, more particularly to a synthesis of a 7-membered carbocyclic compound having diexomethylene groups, a novel compound having the structure represented by the following Chemical Formula 1, from trimethylsilanylmethyl-allenol derivative by the intramolecular Prins cyclization using Lewis acid. The 7-membered carbocyclic compound is a useful intermediate for synthesis of other multicyclic compounds.In Chemical Formula 1, R1is a C1to C6alkyl group, and R2and R3is respectively a hydrogen atom, or R1, R2and R3may be connected with neighboring substituents to form a 5 to 10-membered aliphatic or aromatic ring.

REFERENCES:
Article “The 91stNational Meeting of the Korean Chemical Society”, ISSN 1229-6708, Apr. 18-19, 2003, p. 363.
Fernando Lopez, et al., “Atom-Efficient Assembly of 1,5-Oxygen-Bridged Medium-Sized Carbocycles by Sequential Combination of a Ru-Catalyzed Alkyne-Alkene Coupling and a Prins-Type Cyclization”, J. Am. Chem. Soc. 2002 American Chemical Society, pp. 4218-4219.
Fouzia Machrouhi, “Sequenced Reactions with Samarium(II) Iodide. A Complementary Annulation Process Providing Access to Seven-, Eight-, and Nine-Membered Carbocycles”, J. Org. Chem. 1999 American Chemical Society, pp. 4119-4123.
Gary A. Molander, et al., “Neighboring Group Participation in Lewis Acid-Promoted [3+4] and [3+5] Annulations. The Stereocontrolled Synthesis of Tricylic Ethers”, J. Org. Chem. 1993, American Chemical Society, pp. 5931-3427.
Dale L. Boger, et al., “Thermal, Four-Carbon + Three-Carbon Cycloaddition Reaction of Cyclopropenone Ketals. Total Synthesis of Deacetamidocolchiceine: Formal Total Synthesis of Colchicine”, J. Org. Chem. 1985 American Chemical Society, pp. 3425-3427.
English Translation of I31P121 on Abstract of The 91stNational Meeting of the Korean Chemical Society Program and Abstracts.

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