SYNTHESIS 



The following method of preparing the starting material for 

 this synthesis had been described in igoo by S. Gabriel and J. 

 Colman : ^ 



COx 



CO 

 OH 



CO. 



COOEt 



/N.K 



II N.CH 



NaOMe 



OH 



\y\o^ 



C . CH3 P0CI3 



I — ' 



NH 



C.CH 



I 



N 



3 CH8I + 



NaOMe 



OCH3 



C . CH3 gjj ^ 



\/\c/ 



CI 



0CH3 



ACH. 



.N 



HCl 



/ 



CI 



Another method of synthesis leading to the formation of 

 adermin monomethyl ether was described by S. Morii and K. 

 Makino.^ In this method, the initial step was the same as in 

 the method of Harris and Folkers, and the subsequent stages 

 differed only in detail. 



The synthesis of pyridoxine was protected by the x\merican workers 

 in a series of patents, assigned to Merck & Co. These covered the 

 following series of transformations : 



CHaOEt 



^^y O^n/Vn 



II i 

 CH, 



0,N 



CH^OEt 



N 



CH.OEt 



CH 



PCIb 



H2N 



/\ 



H 



H 



CH 



^\^y 



if 



CN 



CI 



H2N' 



CH 



CHoNH, 



'V 



H2N 



CH 



CH2OH 

 CH2NH2 



CH2OH 



303 



H 

 CH3 



■CHgOH 



1 I 



V 



