^53 



Naphthoquinones 



Mycobacterium, phlei 



Ten mg. were obtained from 450 g. of wet cells. 

 A. F. Brodie, B. R. Davis and L. G. Fieser, /. Am. Chem. 

 Soc. 80 6454 (1958). 



Vitamins K^: 



Vitamin Ko was first isolated from putrefied fish meal In 

 1939 by Doisy and collaborators. Tishler and Sampson 

 later found that it was produced by pure cultures of Bacil- 

 lus brevis. Isler and collaborators corrected the structure 

 originally proposed to A. below. They also isolated a 

 lower isoprenolog, B., from putrefied fish meal. Both 

 structures were proved by synthesis. The later group also 

 determined the structure of (and synthesized) a higher 

 isoprenolog C. isolated earlier in England. 



531 A., CiQH(i^0.2, hght yellow plates, m.p. 54°. 



CHs 



^CH2— CH=C— 



I 

 CH3 



— CH2— CH2— CH=C — 



I 

 CH3 



-CHs 



Bacillus brevis 



R. W. McKee, S. B. Binkley, Sidney A. Thayer, D. W. Mac- 

 corquodale and Edward A. Doisy, J. Biol. Chem. 131 327 

 (1939). 



M. Tishler and W. Sampson, Proc. Soc. Exp. Biol. 68 136 

 (1948). 



532 B., C41H56O2, hght yellow plates, m.p. 50°. 

 O 



CH2— CH=C- 



CH3 



-CH2— CH,— CH=C— 



I 

 CH3 



— CH3 



O. Isler, R. Riiegg, L. Chopard-dit-Jean, A. Winterstein and 

 O. Wiss, Helv. Chim. Acta 41 786 (1958). 



