Biosynthesis inspired Diels-Alder route to pyridines: synthesis of the 2,3-dithiazolylpyridine core of the thiopeptide antibiotics.
Reaction of serine derived 1-alkoxy-2-azadienes with dehydroalanine derived dienophiles results in Diels-Alder reaction and aromatisation to give 2,3,6-trisubstituted pyridines, thereby establishing the viability of the proposed biosynthetic route to the pyridine ring of the thiopeptide antibiotics originally proposed by Bycroft and Gowland.
Moody
Christopher J
CJ
School of Chemistry, University of Exeter, Exeter, UK EX4 4QD. c.j.moody@ex.ac.uk
Hughes
Rachael A
RA
Thompson
Stewart P
SP
Alcaraz
Lilian
L
D000900:Anti-Bacterial Agents / Q000096:biosynthesis* / Q000138:chemical synthesis; D011725:Pyridines / Q000138:chemical synthesis*; D012694:Serine / Q000737:chemistry; D013844:Thiazoles / Q000138:chemical synthesis*; D013883:Thiostrepton / Q000031:analogs & derivatives
D000900:Anti-Bacterial Agents; D011725:Pyridines; D013844:Thiazoles; D012694:Serine; D013883:Thiostrepton