Bycyclic tetrahydrofuran derivatives and process for the...

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

Reexamination Certificate

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C549S396000

Reexamination Certificate

active

11300966

ABSTRACT:
The present invention relates to bicyclic tetrahydrofuran derivatives of Formula (1) and a preparation method thereof, and particularly it relates to a process of preparing compounds of Formula (1) by performing an intramolecular cyclization of tetrahydrofuran-allenol derivatives in the presence of alcohol compound, transitional metal catalyst and carbon monoxide:wherein n is 1 or 2; R is phenyl optionally substituted with C1-C6alkyl, C1-C6alkoxy, hydroxyl or C1-C6hydroxyalkyl group; and R1is C1-C6alkyl group.

REFERENCES:
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Josep Aiguade, Synthesis of a 2,9-Dioxabicyclo[3..3.1]nonane via Double Intramolecular Hetero-Michael Addition: Entry to the F-G Ring System of the Azaspiracids, Org. Lett., 2001, 3, 979-982.
K.C. Nicolaou, Synthesis of the FGHI Ring System of Azaspiracid, Angew. Chem., Int. Ed. 2001,40, 1262-1265.
Stephen Hanessian, Total Synthesis and Structural Confirmation of Malayamycin A: A Novel Bicyclic C-Nucleoside fromStreptomyces malaysiensis, Org. Lett., 2003, 23, 4277-4280.

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