Total synthesis of (-)-uniflorine A.
Total synthesis of (-)-uniflorine A (3) has been accomplished in nine steps and 11% overall yield from carbohydrate-based nitrone 5. The key steps of the synthetic strategy were a high regio- and complete stereoselective 1,3-dipolar cycloaddition of alkene 6 with nitrone 5, a Tamao-Fleming reaction for replacing the silicon substituent with a hydroxy group with retention of configuration, and a Mitsunobu reaction to establish the correct configuration of the target molecule at C-6.
Parmeggiani
Camilla
C
Dipartimento di Chimica Organica Ugo Schiff, Laboratorio di Progettazione, Sintesi e Studio di Eterocicli Biologicamente Attivi (HeteroBioLab), Università di Firenze, via della Lastruccia 13, I-50019 Sesto Fiorentino (FI), Italy.
Martella
Daniele
D
Cardona
Francesca
F
Goti
Andrea
A
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D027842:Syzygium / Q000737:chemistry
D001688:Biological Products; D007212:Indolizines; C487671:uniflorine A