Allen Hanburys Limited

Stanley M Roberts

Roger F Newton

Michael J Dimsdale

David K Rainey

A novel 3-endo-protected hydroxyl-tricyclo[3,2,0,0.sup.2,7 ]heptan-6-one is described which can be alkylated stereospecifically to give a 5-endo-protected hydroxyl-bicyclo[2,2,1]heptan-2-one which may then be converted via a sequence of reactions into prostaglandins of the F-series having a protecting group at the 9-position. The synthesis of the tricyclo[3,2,0,0.sup.2,7 ]heptan-6-one is also described.

3-Endo-protected hydroxyl-tricyclo[3,2,0,0.sup.2,7 ]heptan-6-ones

The invention relates to (1.alpha., 2.alpha., 4.alpha., 6.alpha.)-3-oxatricyclo[4.2.0.0.sup.2,4 ]octane-7-one and derivatives thereof in which the ketone group is protected, which compounds are useful intermediates in the preparation of natural and synthetic prostaglandins. Processes for the preparation of these compounds are described and exemplified as are processes for their conversion into known prostaglandin intermediates.

Novel prostaglandin intermediates

The stereospecific alkylation of a novel 3-endo-protected hydroxyl-tricyclo[3,2,0,0.sup.2,7 ]heptan-6-one is described using a range of lithium-, copper or magnesium-containing organometallic reagents. This reaction provides a 5-endo-protected hydroxyl-bicyclo[2,2,1]-heptan-2-one system from which prostaglandin compounds of the F series having a protecting group at the 9-position hydroxyl group may readily be obtained by a sequence of reactions.

5-Endo-protected hydroxyl-bicyclo[2,2,1]-heptan-2-ones and process for

A novel 3-endo-protected hydroxyl-tricyclo[3,2,0,0.sup.2,7 ]-heptan-6-one is described which can be alkylated stereospecifically to give a 5-endo-protected hydroxyl-bicyclo [2,2,1]heptan-2-one which may then be converted via a sequence of reactions into prostaglandins of the F-series having a protecting group at the 9-position. The synthesis of the tricyclo[3,2,0,0.sup.2,7 ]heptan-6-one is also described.

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Macclesfield, United Kingdom

Stanley M Roberts