Expedient total synthesis of pyrrothine natural products and analogs.
This paper describes an expedient and straightforward total synthesis of the two pyrrothine natural products holomycin (7 steps, 11% overall) and xenorhabdin I (7 steps, 11% overall) and analogs thereof via a common late-stage intermediate. The pathway proceeds via the pyrrothine hydrochloride intermediate (6 steps, 17% overall) which also gave access to very fast synthesis of analogs as demonstrated by the synthesis of , and (7 steps, 11-12% overall).
Hjelmgaard
Thomas
T
Department of Natural Sciences, Bioorganic Chemistry Section, Royal Danish Veterinary and Agricultural University, DK-1871 Frederiksberg C, Denmark.
Givskov
Michael
M
Nielsen
John
J
D000900:Anti-Bacterial Agents / Q000494:pharmacology*; D002625:Chemistry, Organic / Q000379:methods; D002855:Chromatography, Thin Layer; D012321:DNA-Directed RNA Polymerases / Q000378:metabolism; D007769:Lactams / Q000737:chemistry*; D008956:Models, Chemical; D011549:Pseudomonas / Q000378:metabolism; D012329:RNA, Bacterial / Q000096:biosynthesis; D013302:Streptomyces / Q000378:metabolism; D020593:Xenorhabdus / Q000378:metabolism*
D000900:Anti-Bacterial Agents; D007769:Lactams; D012329:RNA, Bacterial; C015265:holomycin; D012321:DNA-Directed RNA Polymerases