One-pot multistep Bohlmann-Rahtz heteroannulation reactions: synthesis of dimethyl sulfomycinamate.
[reaction: see text] 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
MC
School of Chemistry, Main Building, Cardiff University, Park Place, Cardiff, CF10 3AT, United Kingdom. bagleymc@cf.ac.uk
Chapaneri
Krishna
K
Dale
James W
JW
Xiong
Xin
X
Bower
Justin
J
D000900:Anti-Bacterial Agents / Q000737:chemistry; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D013844:Thiazoles / Q000737:chemistry
D000900:Anti-Bacterial Agents; D010455:Peptides; D011725:Pyridines; D011763:Pyrrolizidine Alkaloids; D013844:Thiazoles; C500284:hyacinthacine A2; C049270:sulfomycin; C023666:pyridine