o q u i a , D e p a r t e m e n t o d e Q u i m i c a , AA 1 2 2 6 MEOELLIN.C o l o m b i a C e n t r e d e P h a r m a c o l o g i e e t E n d o c r i n o l a g i e , INSERM-CNRS, 3 4 0 3 3 MONTPELLIER, F r a n c e C37H38N206 ; m l r 3 7 9 . 1 4 5 ( f o u n d ) , 3 7 9 . 1 6 5 ( c a l c . 1 : C22H23N204 ; m l z 1 7 4 .0 5 3 ( f o u n d ) , 1 7 4 .0 5 5 ( c a l c . ) : c10H8N02 : MS ( E I ) m l z ( % ) : 6 0 6 ( 1 1 ) ( M t ' ] , 3 8 0 ( 2 0 1 , 3 7 9 ( 2 9 1 , 3 4 9 ( 1 1 , 1 9 0 ( 6 7 1 , 1 7 4 ( 1 0 0 ) .7 .1 2 ' -0 -a c e t y l -m e d e l l i n e .P r e p a r e d f r o m 1 ( A c 2 0 1 P y r ) .[ e l D -42' ( c = 0 .6 0 , CHC13] ; U V , EtOH, nm ( l o g E ) : 2 2 2 ( 4 .6 0 ) . 2 8 3 ( 3 .9 0 1 ; I R , v , e x , f i l m : 1 7 6 5 , 1 6 0 5 , 1 5 8 0 , 1 5 0 0 cm-' ; 'H-NMR, CDC13, 3 6 0 MHz, 6 ppm : 2 . 1 0 ( s , 3H, O A c -l Z t ) , 2 .3 4 ( 5 , 3H, NMe-2). 2 .6 0 ( s , 3H, N M e -2 ' ) , 3 .7 2 ( 5 , 3H, OMe-121, 3 .8 3 ( s , 3H, O M e -6 ) , 3 .6 0 ( m , I H , H -1 ' 1 , 4 .3 7 ( m , I H , H -I ) , 4 .8 8 a n d 4 .9 4 : AB s y s t e m ( J = 4 H z 1 ( O C H 2 0 ) , 6 .4 1 ( s , 1H, H -5 ) , 6 .9 4 ( 5 , 1H, H -5 ' ) , 6 .6 6 ( s , l H , H -8 ' 1 , 7 .4 9 ( d , 1H, H -l o ) , 6 .7 7 ( d , l H , H -1 3 1 , 7 .2 1 ( d d , I H , H -1 4 ) , 6 .7 3 ( d , I H , H -1 0 ' 1 , 7 .1 5 ( d , I H , H -1 3 ' ) , 7 .3 4 ( d d , 1 H , H -1 4 ' ) ; J10-14=~10,-14,=2 H Z ; J 1 4 -1 3 = J14,-13,=8 Hz ; MS ( E I I m l r ( % ) : 6 4 8 ( 8 4 ) (M ) , 3 8 0 ( 2 2 ) , 3 7 9 ( 6 8 1 , 3 0 7 ( 1 1 1 , 2 3 5 ( 2 4 1 , 1 9 0 ( 9 7 1 , 1 7 0 ( 1 0 0 ) .8 .M. T o m i t a .T .K i k u c h i .K .F u j i t a n i , A. K a t o , H. F u r u k a w a , Y.A o y a g i , M. K i t a n o a n d T .I b u k a , T e t r a h e d r o n L e t t ., 8 5 7 ( 1 9 6 6 ) ; J .B a l d a s , I .R .C .S i c k , 1.I b u k a , R.S. K a p i l a n d Q.N.P o r t e r , J. Chem.S o c .P e r k i n I , 5 9 2 ( 1 9 7 2 ) .9 .K.P. G u h a , B. M