Synthesis of the 2,3,4-trisubstituted indole fragments of nosiheptide and glycothiohexide.
Two routes to the protected 4-hydroxymethyl-3-methylindole-2-carboxylate fragment 17 of the thiopeptide antibiotic nosiheptide are described starting from methyl 4-methylindole-2-carboxylate 11, itself prepared in two steps, or from 3-amino-4-chlorobenzoic acid 26. The first route can be adapted to the synthesis of a fragment of the related antibiotic glycothiohexide-alpha, the 3,4-bis(hydroxymethyl)indole-2-carboxylate in which the two hydroxymethyl groups are differentiated as in indole 19 or the lactone 20.
Bentley
David J
DJ
Department of Chemistry, University of Exeter, Stocker Road, Exeter, UK EX4 4QD.
Fairhurst
John
J
Gallagher
Peter T
PT
Manteuffel
Astrid K
AK
Moody
Christopher J
CJ
Pinder
Joanne L
JL
D004317:Doxorubicin / Q000031:analogs & derivatives* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D013844:Thiazoles / Q000138:chemical synthesis / Q000737:chemistry*
D007211:Indoles; D007783:Lactones; D010455:Peptides; D013844:Thiazoles; C089609:glycothiohexide alpha; C494672:glycothiohexide alpha aglycone; C494673:nocathiacin III; D004317:Doxorubicin; C014134:nosiheptide