Pfizer Handbook of Microbial Metabolites 



486 



HOCH; 



CHO 



OH 



4- CH,— COOH 

 CH3 NH, 



® \X 2H® 



HC C--0 



II i 



HOCHo HC M 



J' .0 



N' 



H CH3 



CH2O 



H© 



NH2 

 HOCH2— CH— COOH 



+ HOCH2— C C 



CHO _.. H' 



H 



HOCH2 



OH ^N^ jO 



H.,o HOCH2 HC M 



HOCHo— C— COOH 



+ 



NHo 



CH. 

 HOCH2 I " OH 



2H© 

 H2O 



CH3 



i® 



CH3 



HOCH — C CO 



li 1 



HOCH. HC M 

 .0 



H"^ CH3 



N' 



H CH3 



CH3— C— COOH 



+ 

 NHa 



H.O 



NH2 

 CH2=C— COOH. 



+ 



CHO 

 HOCH2 I OH 2H® 



H2O 



CH3 



OH© 



H2C-=C C=-0 



HOCH. HC M 

 ,0 



H® CH3 



M = Metal: (T),(2) = Aldol formation and cleavage 

 Ql® — Transamination 

 (3), (5) = «. d-Elimination 



