Efficient approach to fluvirucins B2-B5, Sch 38518, and Sch 39185. First synthesis of their aglycon, via CM and RCM reactions.
A route to fluvirucinins B(2-5) (the common aglycon of fluvirucins B(2)-B(5), Sch 38518, and Sch 39185) is reported for the first time. A ring-closing metathesis (RCM) generated the C6-C7 double bond, which by catalytic hydrogenation (in toluene) gave the desired epimer with a 9:1 diastereoselection. Azide 8a and carboxylic acid 5 came from ethyl-branched fragments C9-C13 (CHO at C9) and C1-C5 via an asymmetric allylation of the former and a cross metathesis (CM) followed by a ketone methylenation (with 20 mol % of DMF as a sacrificial additive) of the latter.
Llàcer
Enric
E
Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, Av. Diagonal 647, 08028 Barcelona, Catalonia, Spain.
Urpí
Fèlix
F
Vilarrasa
Jaume
J
D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D003837:Deoxy Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D015195:Drug Design; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D001386:Azides; D002264:Carboxylic Acids; D003837:Deoxy Sugars; D007769:Lactams; D018942:Macrolides; C094360:fluvirucin B2; C075536:Sch 38518; C075537:Sch 39185