Total synthesis of Phorocantholide J (Posner):
| Reference: | Posner, G. H.; Hatcher, M. A.; Maio, W. A. Org. Lett. 2005, 7, 4301. DOI |
| Reactions: | Ketone enolate+Epoxide • Epoxide+Enolate • Grob fragmentation • EnolSilane → Ketone enolate • Ketone enolate+Oxetane • Lactone-8 • Radical reduction(C-OR) • Alkyl-OH → Alkyl-H(2°) • Barton-McCombie reduction • Lactone-9+ • O-SiMe2tBu → O-H • O-H → O-C(S)OR • EnolSilane → Ketone enolate • |
| Reagents: | Me-Li • Epoxide • BF3·OEt2 • Iodosobenzene-OAc • I2 • Fluoride, R4N+ • S=C(OPh)Cl • HSnBu3 • AIBN • Me-Li • Oxetane • BF3·OEt2 • |