Pfizer Handbook of Microbial Metabolites i88 



i 

 OH COOH OH COOH 



Thus, the acetate and shikimic acid routes to aromatic com- 

 pounds seem to be operating in a single microorganism. 



It was a kind of statistical consideration of the structures of 

 natural products which led to the revival of the acetate hypothe- 

 sis of biogenesis as applied to substances other than fatty acids. 

 Phenolic compounds were particularly instrumental since 

 the frequent occurrence of weta-hydroxyl groups (resorcinol 

 and phloroglucinol types) was easy to recognize and challeng- 

 ing to explain. The case first was stated clearly by Collie many 

 years ago.* Lately Birch and others have developed a firm ex- 

 perimental basis for the theory by isotopic labeling and chemi- 

 cal degradation studies. 



Some phenolic compounds which have been shown in this 

 way to be acetate-derived are : 



6-Methylsalicylic Acid^ 

 Griseofulvin" 

 Mycophenolic Acid" 

 Emodin^ 



*John Norman Collie, Proc. Chem. Soc. 23 230 (1907); idem., }. 

 Chem. Soc. 91 1806 (1907). 



•' A. J. Birch, R. A. Massy-Westropp and C. J. Moye, Australian J. 

 Chem. 8 539 (1955). 



^ A. J. Birch, R. A. Massy-Westropp, R. W. Rickards and Herchel 

 Smith, J. Chem. Soc, 360 (1958). 



" A. J. Birch, R. J. English, R. A. Massy-Westropp, M. Slaytor and 

 Herchel Smith, ibid., 365 (1958); A. J. Birch, R. J. English, R. A. 

 Massy-Westropp and Herchel Smith, ibid., 369 (1958). 



^ Sten Gatenbeck, Acta Chem. Scand. 12 1211 (1958). 



