Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2007-05-29
2007-05-29
McKenzie, Thomas (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C305S136000
Reexamination Certificate
active
11303125
ABSTRACT:
The present invention relates to bicyclic tetrahydrofuran lactone 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-allenic acid derivatives in the presence of a phenyl halide, a palladium catalyst and a base:wherein n is 1 or 2, and R is phenyl optionally substituted with C1–C6alkyl, C1–C6alkoxy, hydroxyl or C1–C6hydroxyalkyl group.
REFERENCES:
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Josep Aiguade, Synthesis of a 2,9-Dioxabicyclo[3.3.1]nonane via Double Intramolecular Hetero—Machael 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.
Peter Somfai, An Enantioselective Total Synthesis of (+)-Altholactone from Diethyl L-Tartrate, Tetrahedron, 1994, 50, 11315-11320.
Patricia Y. Hayes, Total Synthesis and Absolute Stereochemistry of Plakortone D, J. Am. Chem. Soc. 2002, 124,9718-9719.
Cha Joo Hwan
Cho Yong Seo
Koh Hun Yeong
Pae Ae Nim
Shin Chul
Covington Raymond
Frommer Lawrence & Haug LLP;
Korea Institute of Science and Technology
McKenzie Thomas
Santucci Ronald R.
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