Prostaglandin Synthesis by Jasjit Bindra (Auth.)

By Jasjit Bindra (Auth.)

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1 Introduction 25 and PGB refer to the formation of these derivatives from PGE compounds by treatment with acid and base respectively. The chemical relations between PGE, PGF, PGA and PGB compounds are depicted in Fig. 2. The number of double bonds in the molecule are denoted by subscript numerals appearing after the name of the prostaglandin. Thus, prostaglandin E^, F-j, A-j and B-. have only the 13,14-trans double bond. Prostaglandins E2, F2, A2 and B2 have in addition a cis-double bond in the 5,6 position, while prostaglandins Eg, Fg, Ag and Bg carry an additional cis-double bond between the 17,18 position.

Reduction of the ketone function in 7 with excess sodium borohydride followed by ketal hydrolysis with aqueous acid, gave the j3-hydroxy ketone 8. In order to establish the enone structure in 8 it was necessary to effect dehydration of the j3-hydroxy carbonyl under mild enough conditions that would not encourage further elimination of the 11-acetoxy group. This was accomplished by reacting the j3-hydroxyl group with carbodiimide to give a carbamidate derivative which readily underwent cycloelimination ( 9 - H O ) in presence of cupric chloride to give the conjugated enone IO in high yield.

Of special interest to the reader looking for practical laboratory approaches to prostaglandins are the 1,4-conjugate addition (Chapter 7) and Corey's bicycloheptane (Chapter 10) approaches. The A, B, C and D-type prostaglandins are treated individually in Chapters 14 to 17, while methods for converting prostaglandins of one type into another are described in Chapter 18. The isomerie prostaglandins, which frequently arise as side-products of non-stereoselective approaches, and recently, with the discovery of interesting and selective biological activities for some of them, have become synthetic targets in themselves, are discussed in Chapter 19.

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