Optically active epoxycyclohexane derivative and epoxycyclohexan

Details Optically active epoxycyclohexane derivative and epoxycyclohexan Optically active epoxycyclohexane derivative and epoxycyclohexan

1992-02-12

1993-10-19

Evans, Joseph E.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549513, 549539, 549545, C07D30332, C07D30100

Patent

active

052546942

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to an optically active epoxycyclohexane derivative represented by the following general formula (I): ##STR3## wherein R represents a 4-oxycarbonyl-1-hydroxy-3-methyl-3(Z)-buten-1-yl or 4-hydroxycarbonyl-3-methyl-1(E),3(Z)-butadien-1-yl group; and R.sup.1 and R.sup.2 each represent a lower alkoxy group or together form a 1,3-dioxolane ring together with the carbon atoms to which R.sup.1 and R.sup.2 are bonded, derivative represented by the general formula (II): ##STR4## wherein R.sup.3 represents a hydrogen atom or a lower alkyl, allyl, aralkyl or aryl group, which is derived from an optically active epoxycyclohexane derivative represented by the general formula (I), and an enantiomer thereof; and a process for the preparation of a compound represented by the above general formula (I) wherein R is a 4-hydroxycarbonyl-3-methyl-1(E),3(Z)-butadien-1-yl group.
The optically active epoxycyclohexane derivative (I) and its enantiomer and optically active epoxycyclohexanone derivative (II) and its enantiomer according to the present invention serve as important intermediates for the preparation of abscisic acid represented by the following formula (III) which has not been applied to agriculture as yet in spite of its important activity on plant physiology as a plant hormone, so that the utilization thereof in the feature is expected, and xanthoxin represented by the following formula (IV) which is more difficultly available than abscisic acid and therefore has not been applied to agricultural production in spite of its activity equivalent to that of abscisic acid, in the form of a natural type optical isomer or an enantiomer thereof: ##STR5##


BACKGROUND ART

Up to this time, several processes for preparing optically active abscisic acid have been known. These processes are classified into (i) a group of processes characterized by using an optically active raw material (see K. Mori, Tetrahedron Lett., 1973, 2635; M. Shibasaki, S. Terashima and S. Yamada, Chem. Pharm. Bull., 1976, 24, 315; and K. Kienzle, H. Mayer, R. E. Minder and H. Thommen, Helv. Chim. Acta, 1978, 61, 2616), (ii) a group of fermentation processes using a microorganism [see Japanese Patent Laid-Open No. 36393/1983 and the abstracts of the 30th Symposium on the Chemistry of Natural Products (Fukuoka, 1988), p.332 ] and (iii) a group of processes comprising preparing racemic abscisic acid which is not optically active and separating the racemic modification into optically active isomers by optical resolution (see R. S. Burden and H. F. Taylor, Pure & Appl. Chem., 1976, 47, 203).
However, the processes of the group (i) are disadvantageous in that the optically active raw material is generally difficultly available and the fermentation processes of the group (ii) are unfit for practical use owing to their low productivity. The optical resolution processes of the group (iii) have disadvantages due to optical resolution in that the operation is troublesome and the objective optically active substance can be obtained only in a low yield even by following a process using an optically inactive racemic modification of a compound represented by the general formula (VI) or (VII) which will be described below as an intermediate (see M. G. Constantino, P. Losco and E. E. Castellano, J. Org. Chem., 1989, 54, 681), which process is one of the most efficient processes among known processes for preparing a racemic modification.
Although optically active abscisic acid is demanded because of its higher activity as a plant hormone than that of racemic one (see R. S. Burden and H. F. Taylor, Pure & Appl. Chem., 1976, 47, 203), optically active abscisic acid is now much more expensive than racemic one.
On the other hand, not a few processes for preparing xanthoxin have also been known. For example, there have been known a process (i) characterized by using .beta.-ionone as a starting material (see R. S. Burder, G. W. Dawson and H. F. Taylor, Phytochem., 1972 11, 2295 and H. F. Taylor and R. S. Burder, J. Exp. Bot., 1973, 2

REFERENCES:
patent: 3400158 (1968-09-01), Roberts
patent: 3567743 (1971-03-01), Anderson
Acemoglu et al. "Helvetica Chimica Acta" vol. 71, No. 5, (1988), pp. 931-956.

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