One-pot multistep Bohlmann-Rahtz heteroannulation reactions: Synthesis of dimethyl sulfomycinamate
(Chemical Equation Presented) The synthesis of dimethyl sulfomycinamate, the acidic methanolysis product of the sulfomycin family of thiopeptide antibiotics, from methyl 2-oxo-4-(trimethylsilyl)but-3-ynoate is achieved in a 2,3,6-trisubstituted pyridine synthesis that proceeds with total regiocontrol in 13 steps by the Bohlmann-Rahtz heteroannulation of a 1-(oxazol-4-yl)enamine or in 12 steps and 9% yield by three-component cyclocondensation with N-[3-oxo-3-(oxazol-4-yl)propanoyl]serine and ammonia in ethanol.
Bagley, Mark C.,Chapaneri, Krishna,Dale, James W.,Xiong, Xin,Bower, Justin
p. 1389 - 1399
(2007/10/03)
Synthesis of Dimethyl Sulfomycinamate
(Equation presented) Dimethyl sulfomycinamate, the oxazole-thiazole- pyridine product generated in the methanolysis of the thiopeptide antibiotic sulfomycin I, is prepared in 13 steps and 8% overall yield by the Bohlmann-Rahtz heteroannulation of 1-(oxazol-4-yl)enamines and methyl 4-(trimethylsilyl)-2-oxobut-3-ynoate.
Bagley, Mark C.,Dale, James W.,Xiong, Xin,Bower, Justin
p. 4421 - 4424
(2007/10/03)
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