The details of a total synthesis of methoxatin (1), the coenzyme of several bacterial alcohol dehydrogenases, are presented.Methoxatin has been prepared in 13 steps by starting from 2,3-dimethoxytoluene.The successful synthetic strategy for construction of the coenzyme used a Pfitzinger synthesis for preparation of the quinoline dicarboxylic acid portion of 1 and an "umpolung" variation of the Reissert indole synthesis for annulation of the remaining pyrrole ring.
Gainor, James A.,Weinreb, Steven M.
p. 2833 - 2837
(2007/10/02)
Preparation and Catalytic Hydrogenation of 4,6-Dimethyl- and 4,7-Dimethyl-8-methoxycoumarins. A 4-Methyldihydrocoumarin Synthesis
Reduction of the title coumarins at 1500 psi and 150 deg over 10percent palladium on charcoal provides a simple route to dihydrocoumarins and/or ethylbutanoates, hydrogenolysis products of the lactone.Lower pressures and temperatures tend to yield only th
Mills, Frank D.
p. 1597 - 1600
(2007/10/02)
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