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.
School of Chemistry, University of Exeter, Exeter, UK EX4 4QD. c.j.moody@ex.ac.uk
Christopher J
CJ
Moody
Rachael A
RA
Hughes
Stewart P
SP
Thompson
Lilian
L
Alcaraz
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