Die Benzoesäurederivate (Ia) und die Zimtsäure‐derivate (Ib) reagieren mit N‐Hydroxysuccinimid zu den Verbindungen (II), die mit GIycin zu den N‐Acylglycinen (III) umgesetzt werden.
3‐Alkyl‐1,2,4‐cyclopentanetriones can readily be converted to all trans 2,3‐dialkyl‐1,4‐cyclopentanediols. The latter compounds are intermediates for the synthesis of a prostanoid synthon, known as Corey's lactone, when the alkyl substituents contain appropriate functional groups. The conversion of two different sets of side‐chains to readily distinguishable two‐carbon and one‐carbon aldehyde units is described. Extensive 1H‐NMR data are included.
A C I O BY TREATMENT WITH B O I L I N G HYDROCHLORIC A C I OW . V a n B r u s s e l , 0 . T a v e r n i e r X a n d C . F . Van S u m e r e L a b o r a t o r y o f P l a n t B i o c h e m i s t r y U n i v e r s i t y o f G h e n t K . L . L e d e g a n c k s t r . 3 5 8 -9 0 0 0 -G h e n t , B e l g i u m Received 4/4/78 -Accepted 2 6 / 4 / 7 8 . ABSTRACT P r e v i o u s e x p e r i m e n t s s h o w e d t h e i n s t a b i l i t y o f h y d r o x y c i n n a m i c a c i d s ( e . g . f e r u l i c a c i d 1 i n a c i d m e d i a . I n o r d e r t o s t u d y t h i s p r o b l e m , w h i c h i s o f g r e a t i m p o r t a n c e f o r t h e a n a l y s i s o f n a t u r a l l y o c c u r r i n g h y d r o x y c i n n a m i c a c i d d e r i v a t i v e s . m o r e t h o r o u g h l y , f e r u l i c a c i d w a s t r e a t e d o n a p r e p a r a t i v e s c a l e w i t h b o i l i n g h y d r o c h l o r i c a c i d a n d t h e d e c o m p o s i t i o n p r o d u c t s o b t a i n e d w e r e s e p a r a t e d a n d i d e n t i f i e d .
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Die Reduktion der Tri= äthoxy‐cyclopentenone (I) mit Lithiumaluminiumhydrid in siedendem Tetrahydrofuran führt zu einem Gemisch aus 2‐Hydroxy‐cyclopentenonen (II) als Hauptprodukt und 3,5‐Dioxocyclopentenen (III).
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