Ti(III)-promoted radical cyclization of epoxy enones. Total synthesis of (+)-paeonisuffrone.
The total synthesis of (+)-paeonisuffrone starting from (+)-10-hydroxycarvone is described. The key step of our synthetic strategy is a titanium-catalyzed stereoselective cyclization initiated by epoxide opening through electron transfer. This reaction stereoselectively affords the highly oxygenated pinane skeleton present in the target molecule and opens a new and effective approach to the synthesis of the complex, biologically active terpenoids isolated from the roots of the Chinese paeony (Paeonia albiflora Pallas and Paeonia suffruticosa Andrews).
Martín-Rodríguez
María
M
Departamento de Química Orgánica, Universidad de Salamanca, 37008 Salamanca, Spain.
Galán-Fernández
Raquel
R
Marcos-Escribano
Andrés
A
Bermejo
Francisco A
FA
D002384:Catalysis; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry*; D039821:Monoterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry; D014025:Titanium / Q000737:chemistry*
D004852:Epoxy Compounds; D039821:Monoterpenes; D009942:Organometallic Compounds; D013729:Terpenes; C419234:paeonisuffrone; D014025:Titanium