Process for the production of a cyclopentenol derivative

Details Process for the production of a cyclopentenol derivative Process for the production of a cyclopentenol derivative

1994-06-02

1996-08-27

Ivy, C. Warren

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549475, 556465, 556466, 556489, 568838, C07C 3506, C07D30702, C07F 708

Patent

active

055502601

ABSTRACT:
A process for the production of a cyclopentenol compound represented by the formula I: ##STR1## wherein R.sub.1 represents a 2-propenyl group or a 2-propynyl group from a cyclopentenolone compound represented by the formula II: ##STR2## by protecting the hydroxyl group of the compound II, reacting the protected compound II with a reagent system obtained from TiCl.sub.4, Zn and CH.sub.2 Br.sub.2 or CH.sub.2 I.sub.2 and removing the protecting group from the resulting reaction product.

REFERENCES:
patent: 4304733 (1981-12-01), Martel et al.
patent: 4356187 (1982-10-01), Martel et al.
Bull. Chem. Soc. Jpn.,vol. 53, No. 6, 1698-1702 (1980), K. Takai et al., "Wittig-type Reaction of Dimetallated Carbodianion Species as Produced by Zinc Reduction of gem-Polyhalogen Compounds in the Prsence of Lewis Acids".
Tetrahedron Letters, vol. 23, No. 41, pp. 4293-4296, 1982, L. Lombardo, "Methylenation of Carbonyl Compounds with Zn-CH.sub.2 Br.sub.2 -TiCl.sub.4 ".
Tetrahedron Letters, vol. 25, No. 10, pp. 1067-1070, 1984, Y. Ogawa et al., "The Intramolecular Thermal ENE Reaction Route to (+)-9(0)-Methano-.increment..sup.6*9a) -PGI.sub.1 ".
J. Org. Chem., vol. 55, No. 13, pp. 4051-4063, 1990 (the left column on p. 4058, R. Jacobs et al.,"Defense Mechanisms of Arthropods. 84. Synthesis of (-)-a-Necrodol and (-)-.beta.-Necrodol: Novel Cyclopentanoid Terpenese from a Carrion Beetle".
J. Org. Chem., vol. 48, No. 13, pp. 2298-2300, 1983, L. Lombardo et al., "A New Strategy for C.sub.20 Gibberellin Synthesis: Total Synthesis of (.+-.)-Gibberellin A.sub.38 MEthyl Ester".
Tetrahedron Letters, vol. 26, No. 45, pp. 5579-5580, 1985, J. Hibino et al., "Carbonyl Methylenation of Easily Enolizable Ketones".
Org. Synth., 65, 81 (1987), pp. 81-89, L. Lombardo et al., "Methylenation of Carbonyl Compounds: (+)-3-Methylene-cis-p-Methane (Cyclohexane, 4-methyl-2-methylene-1-(1-methylethyl)-, R,R-)".
Tetrahedron Letters, No. 27, 1978, Oxford GB, pp. 2417-2420, K. Takeai et al.,"Effective Methods of Carbonyl Methylenation".
Tetrahedron Letters, No. 45, 1985, Oxford, GB, pp. 5581-5584, T. Okazoe et all,"Chemoselective Methylenation with a MEthylenedianion Synthon".

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