Claims
- 1. A process for the preparation of 1R, cis compounds in all their possible isomeric forms of the formula ##STR57## wherein W is hydrogen when Y is --COOR' or --COSR' and W is halogen when Y is --COOR' and R' is selected from the group consisting of (1) hydrogen, tert.-butyl, --CH.sub.2 OCH.sub.3, benzyl and --CH.sub.2 --SCH.sub.3 with the double bond having Z configuration when W is hydrogen and the E configuration when W is halogen comprising reacting the lactone of cis 2,2-dimethyl-3-dihydroxymethyl-cyclopropane-1-carboxylic acid in the presence of a strong base with a phosphorane of the formula ##STR58## wherein C, D, E, F, G AND G.sub.1 are selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms to obtain the corresponding compound of formula I with the cyclopropane and carboxy of Y both being in the 1R cis position with respect to the double bond.
- 2. The process of claim 1 wherein C and E are hydrogen and D and F are methyl.
- 3. The process of claim 1 wherein the reaction is effected at -10.degree. to +25.degree. C.
- 4. The process of claim 1 wherein the reaction is effected on a solvent selected from the group consisting of tetrahydrofuran, dimethylformamide, dimethylsulfoxide, hexamethylphosphoretriamide and dimethoxyethane and mixtures thereof with aliphatic or aromatic hydrocarbons.
- 5. A process of claim 1 wherein the compound of formula III has the formula ##STR59## to obtain a compound of the formula ##STR60## wherein the double bond has the Z configuration.
Priority Claims (1)
Number |
Date |
Country |
Kind |
82 07870 |
May 1982 |
FRX |
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PRIOR APPLICATION
This application is a continuation of U.S. patent application Ser. No. 120,868 filed Nov. 16, 1987 which is a continuation of U.S. patent application Ser. No. 808,845 filed Dec. 12, 1985 which is a continuation of U.S. patent application Ser. No. 491,013 filed May 3, 1983, all now abandoned.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
4312817 |
Martel et al. |
Jan 1982 |
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Non-Patent Literature Citations (1)
Entry |
Breuer et al., Tetrahedron, vol. 34, No. 7, pp. 997-1002, Pergamon Press (1978). |
Continuations (3)
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Number |
Date |
Country |
Parent |
120868 |
Nov 1987 |
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Parent |
808845 |
Dec 1985 |
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Parent |
491013 |
May 1983 |
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