Patent ID: 8993762
Filing Date: 2015-03-31
Classification: C07D

Abstract:
1. A method for the synthesis of a thaxtomin or analog thereof having the structure (I) wherein R1 is NO 2 and R2 is selected from a lower alkyl, hydroxyl, halogen, fluoromethyl, difluoromethyl, trifluoromethyl, nitro, amine, methoxy, fluoromethoxy, difluoromethoxy, and trifloromethoxy, comprising: (a) reacting a tryptophan amide analog having the structure with substituted phenyl acrylic acid having the structure wherein R is selected from a lower alkyl, hydroxyl, halogen, fluoromethyl, difluoromethyl, trifluoromethyl, nitro, amine, methoxy, fluoromethoxy, difluoromethoxy, and trifloromethoxy, or its keto tautomer to obtain a compound having the structure (A2) wherein R1 is NO 2 and R2 is selected from a lower alkyl, hydroxyl, halogen, fluoromethyl, difluoromethyl, trifluoromethyl, nitro, amine, methoxy, fluoromethoxy, difluoromethoxy, and trifloromethoxy; and (b) subjecting the compound having the structure (A2) to a cyclization agent to obtain the structure (I).