Pfizer Handbook of Microbial Metabolites 



156 



synthetic process, apparently arises from phosphorylated meva- 

 lonic acid by a concerted decarboxylation with elimination of 

 the C-3-hydroxyl group, since it has been shown that no proto- 

 nation of the carbon chain occurs during decarboxylation/° 



CH3 



HOCH2— CH2— C— CH2— COOH 



I 

 OH 



Mevalonic Acid 



Mevalonic 

 Acid 



Mevalonic 

 Acid 



5-Monophosphate 5-Pyrophosphate 



Mevalonic 



Acid 

 3-Phosphate- 

 5-Pyrophosphate 



00 CH3 O ' 



T T I ^--N II ^Q 



HO— P— O— P— O— CH2— CH2— C— CH2— C— O ^ 



I 



OH OH 



OH 



HO— P— O— P— OH 



I i 



o o 



Mevalonic Acid Dipyrophosphate 



00 ^ CH3 



T T I 



HO— P— O— P— O— CH2— CH2— C=CH2 



I I 



OH OH 



Isopentenyl Pyrophosphate 



Since both y,y-dimethylallyl pyrophosphate^^ and farnesyl 

 pyrophosphate^^ have been Isolated, it is possible to envisage a 

 continuation : 



H3O6P2O— CH2 



H3O6P2O 



e 



CH, 



®< 



Isopentenyl 

 Pyrophosphate 



N 



CH2— OP2O6H3 



\ 



Dimethylallyl 

 Pyrophosphate 



Isopentenyl 

 Pyrophosphate 



^° A. de Waard, A. H. Phillips and Konrad Bloch, /. Am. Chem. 

 Soc. 81 2913 (1959). 



11 B. W. Agranoff, H. Eggerer, U. Henning and F. Lynen, 7- Am. 

 Chem. Soc. 81 1254 (1959). 



^2 F. Lynen, H. Eggerer, U. Henning and Ingrid Kessel, Angew. 

 Chem. 70 738 (1958). 



