One-Pot Multistep Bohlmann-Rahtz Heteroannulation Reactions: Synthesis of Dimethyl Sulfomycinamate

Bagley, Mark Christopher, Chapaneri, Krishna, Dale, James W., Xiong, Xin and Bower, Justin 2005. One-Pot Multistep Bohlmann-Rahtz Heteroannulation Reactions: Synthesis of Dimethyl Sulfomycinamate. The Journal of Organic Chemistry 70 (4) , pp. 1389-1399. 10.1021/jo048106q

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Abstract

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.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Schools > Chemistry
ISSN:	00223263
Last Modified:	19 Mar 2016 22:03
URI:	https://orca.cardiff.ac.uk/id/eprint/1426

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