SYNTHESIS AND THE SPECTRAL-ANALYSIS OF 4-[1-ACETAMIDO-3-(3,4,5-TRIMETHOXYPHENYL)PROPYL]-2-METHOXYTROPONE AND 6-[1-ACETAMIDO-3-(3,4,5-TRIMETHOXYPHENYL)PROPYL]-2-METHOXYTROPONE (B-RING-OPEN ANALOGS OF COLCHICINE)

The treatment of 4- left bracket 1-acetamido-3-(3,4,5-trimethoxyphenyl)propyl right bracket tropolone with etheral diazomethane gave the 6- and 4-substituted title compounds in 51 and 38% yields, respectively. The 270-MHz **1H-NMR spectral analysis performed on these compounds, colchicine, and two methyl ethers of hinokitiol permits unequivocal assignment of the position of the C-substituent on these 2-methoxytropone rings. Attempts were made to effect the direct B-ring closure of these intermediates and 4- left bracket 1-acetamido-3-(3,4,5-trimethoxyphenyl)propyl right bracket -5-aminotropolone using various oxidizing reagents.