Prostanoids chemistry

Steroid chemistry, the glamor area of natural product research in the years following World War II, was replaced by macrolides, alkaloids, and prostanoids. Sterol chemistry again became exciting when an unanticipated rich diversity of marine invertebrate sterols were isolated, notably from sponges. After pioneering research in Italy, the field was reborn in Carl Djerassi s laboratory at Stanford. As a result, we now have a better and more detailed knowledge of sterol biosynthesis than of any other class of marine natural products. The authors of Chapter 1 are Stanford alumni. 

Investigations of the natural products chemistry of the Red Sea soft coral Lobophyton depressum (Alcyonacea) led to the isolation of a crystalline prostanoid derivative [70]. On the basis of H NMR data, the planar structure was developed as methyl ll-acetoxy-PGF2tt (56). Stereochemistry at Cl5 was established as S by comparison of the biological and NMR features of the hydrolyzed... 

Selective fluorination of prostanoids has been effected on the cyclopentane nucleus and on both side chains. A variety of techniques have been employed but may be arbitrarily divided into the fluorination reactions of intermediates and the use of fluorinated building blocks to prepare the target compounds. The chemistry and biology of fluorinated prostaglandins, prostacyclins and thromboxanes through 1981 has been reviewed (110). 

Efficiency in the synthesis of prostanoids has been an important aspect of organic chemistry for over two decades. Because the prostaglandins are chiral, synthesis of enantiopure drugs is highly desirable for clinical applications. The following examples of prostaglandin synthesis are taken from the work of Corey, much of which is summarized in Chapter 11 of his recent book [239]. The hydroxy acid shown in Scheme 6.52a has been used as a key intermediate in a number of... 

Coleman, R.A., Kennedy, I., Humphrey, ERA., Bunce, K., and Fumley, R (1990). Prostanoids and their receptors, in Comprehensive Medicinal Chemistry, J.C Emmett, Ed., Oxford, U.K. Pergamon Press, 3 643-714. 

The last chapter of the book explores in depth an important new area — prostanoid bronchodilator drugs. An extensive review of the chemistry and structure-activity relationships of the prostaglandin bronchodilators is presented for the first time and prospects for a useful clinical agent are discussed. 

Muchowski, J.M., "Chemistry, Biochemistry and Pharmacological Activity of Prostanoids", Pergamon Press, Oxford, (1979), page 39. 

Yamamoto, S. (1988) Characterization of Enzymes in Prostanoid Synthesis, in Prostaglandins Biology and Chemistry of Prostaglandins and Related Eicosanoids (Curtis-Prior, P.B., ed.) pp. 37-51, Churchill Livingstone, Edinburgh. 

PACE ASCIAK CR The 6 [ 9 ] oxy cyclase pathway of prostaglandin endoperoxide metabolism, in Chemistry, biochemistry and pharmacological activity of prostanoids, Roberts SM, Scheinmann F (eds),... 

Prostaglandins.—It is clear that total syntheses are often used to develop novel ideas in chemistry. An explicit example has come from Trost et al in their enantioconvergent approach to prostanoids. Thus the olefinic acids (17) and (18) are mirror images which may be interconverted by allylic rearrangement. By choosing an optically active R a pair of diastereoisomers results which can be separated. The unwanted isomer can then be equilibrated with the desired isomer so that theoretically a 100% conversion into one enantiomer may be achieved,... 

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