Bicyclo[3,3,0]octan-3-ones

Details Bicyclo[3,3,0]octan-3-ones Bicyclo[3,3,0]octan-3-ones

1985-03-18

1986-11-11

Fan, Jane T.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549305, 549214, 560121, 562503, 564189, 568379, C07D30793

Patent

active

046224106

ABSTRACT:
The present invention relates to intermediates of the general formula: ##STR1## (wherein Y and Z, which may be the same or different, each represents a trans-vinylene group or an ethylene group, R.sup.2 represents a hydrogen atom or a methyl or ethyl group, R.sup.3 represents a single bond or an alkylene group of 1 to 5 carbon atoms, R.sup.4 represents an alkyl group of 1 to 8 carbon atoms, a cycloalkyl group of 4 to 7 carbon atoms unsubstituted or substituted by at least one alkyl group of 1 to 8 carbon atoms or a phenyl or phenoxy group unsubstituted or substituted by at least one halogen atom, trifluoromethyl group or alkyl group of 1 to 4 carbon atoms, R.sup.5 represents a hydroxy- protecting group which can be removed in acidic conditions and W.sup.1 represents a group of the formula: --COOR.sup.1, --CON(R.sup.6).sub.2, --CH.sub.2 OR.sup.5 or --CH(OR.sup.7)CH.sub.2 OR.sup.5 (in which R.sup.1 represents a hydrogen atom or an alkyl group of 1 to 12 carbon atoms, the groups R.sup.6, which may be the same or different, each represents an alkyl group of 1 to 4 carbon atoms, a phenyl group or an aralkyl group of 7 to 12 carbon atoms or R.sup.7 represents an acyl group of 2 to 12 carbon atoms and R.sup.5 is as hereinbefore defined) with the proviso that, when R.sup.3 represents a single bond, R.sup.4 does not represent a substituted or unsubstituted phenoxy group, which are useful in the preparation of 6-keto-prostaglandin derivatives.

REFERENCES:
patent: 4558142 (1985-10-01), Holland et al.
Tetrahedron Letters, vol. 25, 21, pp. 2199-2200 (1984)--this article was published on 8th May, 1984, after the priority date of the present application which is 19th Mar. 1984--The Synthesis of 2,3-Dinor-6-Oxo-Prostaglandin F.sub.2.alpha. from a Prostaglandin Lactone Intermediate, and the Reaction Scheme Produces 2,3-Dinor-6-Oxo-PGF.sub.1.alpha., but no Other 6-Keto-PG.

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