Method for the preparation of lariciresinol...

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

Reexamination Certificate

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C568S633000, C568S644000, C568S652000

Reexamination Certificate

active

07049449

ABSTRACT:
A method for the preparation of lariciresinol, cyclolariciresinol or secoisolariciresinol, which method includes the steps of a) reducing hydroxymatairesinol to give 7-hydroxy-secoisolariciresinol, and b) subjecting the 7-hydroxy-secoisolariciresinol obtained in step a) to i) cyclization to give lariciresinol, or ii) cyclization to give cyclolariciresinol, or iii) catalytic hydrogenolysis to give secoisolariciresinol.

REFERENCES:
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patent: WO 97/14670 (1997-04-01), None
patent: WO 00/59946 (2000-10-01), None
Umezawa et al, “Synthesis of lariciresinols”, (1994) vol. 121 No. 157395, abstract best avaiible.
Freudenberg et al., “Die Lignane Des Fichtenholzes,” 90Chemische Berichte Jahrg.2857-2869 (1957).
Okunishi et al., “Enantiomeric Compositions and Biosynthesis of Wikstroemia Sikokiana Lignans,” 46J. Wood Sci234-242 (2000).
Moritani et al., “A Highly Stereoselective Synthesis of 3-hydroxy-1-aryltetralin Lignans Based on the Stereoselective Hydroxylation of α,β-dibenzyl-γ-butyro-lactones: The First Synthesis of (±)-cycloolivil,” 1J. Chem. Soc., Perkin Trans.2747-2753 (1996).
Buckleton et al., “Oxidative Coupling of Lignns, II* Non-Phenolic Coupling of Diarylbutane Lignans Related to Matairesinol Dimethyl Ether,”Australian Journal of Chemistry305-324 (1987).
Kawamura et al., “Photodiscoloration of Western Hemlock (Tsuga Heterophylla) Sapwood III* Early Stage of Photodiscoloration Reaction with Lignans,” 44J. Wood Sci47-55 (1998).

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