Process for preparing polyprenols

Details Process for preparing polyprenols Process for preparing polyprenols

1998-04-27

1999-11-09

Wilson, James O.

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

568700, 568714, 568865, 514724, 514739, C07C 3302

Patent

active

059818115

ABSTRACT:
A process for the preparation of a polyprenol represented by formula (1): ##STR1## where Y and Z individually represent a hydrogen atom or are coupled together to form a carbon-carbon bond; R represents a hydrogen atom or a protective group for a hydroxyl group, and n is 0 or an integer not less than 1, by reacting an organic complex of an alkali metal with a compound represented by formula (2): ##STR2## where either V represents a halogen atom, while W and X are coupled together to form a carbon-carbon bond, or X represents a halogen atom, while V and W are coupled together to form a carbon-carbon bond; A represents a protective group for a hydroxyl group, and Y, Z and n are as defined above.

REFERENCES:
patent: 4839389 (1989-06-01), Koyama et al.
patent: 5714645 (1998-02-01), Asanuma et al.
N. Ya. Grigor Eva, et al, Bulletin of the Academy of Sciences of the USSR. Division of Chemical Science, vol. 35, No. 11, Part 1, pp. 2300-2306, "Reaction of Isoprenoid Olefins With SeO.sub.2 in Aprotic Solvents", Nov. 1986.
Journal of the American Chemical Society; 92:14, Jul. 15, 1990, p. 4463.
Faulkner et al; "Application of the Claisen Rearrangement to Thesynthesis of Trans Trisubstituted Olefinic Bonds. Synthesis of Squalene and Insect Juvenile Hormone", Journal of the American Chemical Society/95:2/Jan. 24, 1973, pp. 553-563.
Okano et al., "Counter" Phase Transfer Catalysis of Water-Soluble Phosphine Complexes. Catalyitic Reduction of Allyl Chlorides and Acetates with Sodium Formate in Two-Phase Systems ; The Chemical Society of Japan; Chemistry Letters, pp. 1463-1466 (1986).
Hutzinger et al, "Stereospecific Reduction and Cross-Coupling of .gamma.-Monosubstituted Llylic Chlorides Using Coordinatively Unsaturated Palladium Catalysts", J. Org. Chem. 1991, 56, 2916-2920.

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