Chemistry, Biochemistry, and Pharmacological Activity of by Stanley M. Roberts and Feodor Scheinmann (Eds.) PDF

By Stanley M. Roberts and Feodor Scheinmann (Eds.)

ISBN-10: 0080237991

ISBN-13: 9780080237992

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Extra info for Chemistry, Biochemistry, and Pharmacological Activity of Prostanoids. Including the Proceedings of a Symposium on the Chemistry and Biochemistry of Prostanoids Held at The University of Salford, England, 10–14 July 1978

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L. Caton et oJ. 32 The 2-alkycyclopent-2-enone ii>-carboxylic a c i d 17 r e q u i r e d f o r synthesis of 1 0 hydroxyprostaglandins by t h i s approach i s a very w e l l known prostaglandin i n t e r ­ mediate which was conveniently prepared here by o x i d a t i o n w i t h Jones reagent of the 7-hydroxyheptyl compound 1 . p. 6 2 - 4 ° . p. 6 1 - 3 , the t e t r a h y d r o p y r a n y l ether 21 of which was t r e a t e d w i t h the copper l i t h i u m complex 13 i n ether a t ca -20° f o r 1 hour to form 22.

D e r i v a t i v e s were e a s i l y o b t a i n a b l e by t h e above t e c h n i q u e s , i t o c c u r r e d t o us t h a t i t o u g h t t o b e p o s s i b l e t o u s e t h e 1 1 - h y d r o x y group i n t h e s e compounds t o e f f e c t an i n t r a m o l e c u l a r d e l i v e r y o f h y d r i d e i o n t o t h e c a r b o n y l g r o u p a t C-9. The s u c c e s s o f s u c h a p r o c e s s w o u l d b e c o n t i n g e n t upon t h e u s e o f a r e a g e n t w h i c h w o u l d h a v e a minimum o r n o e f f e c t o n o t h e r r e d u c i b l e g r o u p s i n the substrate.

C. J. Coffee, G. Darnbrough, M. N. Palfreyman and T. , D a g e n h o m , Essex, RMIO 7XS I n e a r l i e r c o m m u n i c a t i o n s f r o m t h i s l a b o r a t o r y we p u b l i s h e d s y n t h e s e s o f ( + ) 11-deoxyprostaglandins of the and F^^ s e r i e s b y r o u t e s b a s e d on t h e e l a b o r a t i o n of 2-(7-hydroxyheptyl) cyclopent-2-enone (1): T h i s a p p r o a c h h a s b e e n u s e d t o s y n t h e s i s e many 1 1 - d e o x y p r o s t a g l a n d i n a n a l o g u e s f o r b i o l o g i c a l e v a l u a t i o n a n d we h e r e d e s c r i b e t w o a r e a s i n \ ^ i i c h t h e w o r k h a s b e e n d e v e l o p e d a f f o r d i n g 1 0 - h y d r o x y - and Ü - c h a i n a r y l - 1 1 - d e o x y p r o s t a ^ l a n d i n s .

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Chemistry, Biochemistry, and Pharmacological Activity of Prostanoids. Including the Proceedings of a Symposium on the Chemistry and Biochemistry of Prostanoids Held at The University of Salford, England, 10–14 July 1978 by Stanley M. Roberts and Feodor Scheinmann (Eds.)


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