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Production of cyclopentane derivatives
| Details |
Inventors: Matsui, Masanao; Katsube, Junki; Shimomura, Hiromi; Murayama, Eichi;
Assignee: Sumitomo Chemical Co., Ltd. (Osaka, JA)
Primary Examiner: Brust; Joseph P.
Assistant Examiner:
Attorney, Agent or Firm: Sughrue, Rothwell, Mion & Zinn
Cyclopentane derivatives of the formula ##SPC1## Wherein R.sup.1 is a group of the formula --(CH.sub.2).sub.n --X in which X is a carboxyl group or its homologue, a halogen atom or a hydroxyl group and n is an integer of from 1 to 7; Y.sup.1 is a formyl group of a carboxyl group or its homologue; and Z.sup.1 is a formyl group, a carboxyl group, a hydroxymethyl group, an acetyl group, an acetoxy group, or a hydroxyl group and a process for their preparation are disclosed. The process schematically comprises the Diels-Alder reaction of a compound having the formula R.sup.1 --CH=CH--Y.sup.1 with cyclopentadiene followed by oxidation of the bicycloheptene reaction product formed into a cyclopentane derivative in which Z.sup.1 is a formyl group, a hydroxymethyl group or a carboxy group. Subsequent conversion of this cyclopentane derivative by methylation into a diacetyl cyclopentane compound followed by peroxidation and hydrolysis results in the production of a series of cyclopentane derivatives which are useful, for example, as intermediates for the production of prostaglandins. |
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DETAILED DESCRIPTION OF THE INVENTION The process of the present invention will now be described below stage by stage.
STAGE 1 Production of Novel Bicycloheptene Derivatives of the Formula (III) The bicycloheptene derivatives of the formula (II) ##SPC12## prepared in this stage are novel compounds except the case in which R.
sup.
1 is a halomethyl group, and are obtained by reacting the compounds of the formula (III) r.
sup.
1 --ch=ch--y.
sup.
1 (iii) with cyclopentadiene to form diene-adducts using the Diels-Alder reaction.
The compound of the formula (III) and cyclopentadiene may be directly mixed with each other to perform the reaction, but it is also possible to react them in an inert solvent, such as ether, benzene, toluene, xylene, methanol, ethanol, propanol, acetic acid or methylene chloride.
The reaction temperature is optional and can range from 0.
degree.
to 200.
degree.
C, but generally it is better to promote the reaction by heating.
The ratio of the compound of the formula (III) to cyclopentadiene used in the reaction is optional and can range from 10:1 to 1:10.
The bicycloheptene derivative so obtained may be separated and purified by conventional methods such as chromatography and distillation.
The bicycloheptene derivative is considered to include four stereoisomers (diastreomers).
This stereoisomerism is strongly restricted by the type of geometrical isomerism (trans and cis) of the starting compound of the formula (III).
The stereosiomers may, if desired, be separated by known means, such as column chromatography as gas chromatography.
Most of the starting compounds of the formula (III) are novel compounds which are synthesized by the inventors of the present invention using several procedures; some examples of them are illustrated as follows: ##EQU1## STAGE 2 Production of Novel Cyclopentane Derivatives of the Formula (Ia) The novel cyclopentane derivatives of the formula (Ia) ##SPC13## are produced by oxidizing the bicycloheptene derivatives of the formula (II), obtained in Stage 1, with ozone or other oxidizing agents to cleave the double bond
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Vasodialators 
