Experiments on the synthesis of tetracycline. Part VIII. An attempted total synthesis of 4-hydroxy-6-methylpretetramid
Abstract
The use of a 1,2,4-trimethoxy-ring A component in producing the tetracycline analogue 12-ethylenedioxy-5,5aα,6,11,11aα,12-hexahydro-6β,10-dihydroxy-1,3,4-trimethoxy-6α-methyl-11-oxonaphthacene-2-carbox-amide (XX; R = H) is described. This potential tetracycline precursor is converted into 6-methylpretetramid, which itself has been oxidised to 4-hydroxy-6-methylpretetramid.