Total synthesis of Archazolid A (Part 2):
| Reference: | Menche, D.; Hassfels, J.; Li, J.; Mayer, K.; Rudolph, S. J. Org. Chem. 2009, 74, 7220. DOI (Part 1) |
| Reactions: | EnoateEster → Allyl-OH • Allyl-OH → Enal • CarboxEster → EnolBorane • CarboxEster → Carboxamide • Abiko-Masamune Aldol • Aldol-BR2 → Aldol • CarboxEster enolate+Aldehyde • O-H → O-Me • O-PMB → O-H • Carbene • CarboxEster enolate+Alkyl-X • Alkyl-X+Enolate • Decarboxylative elimination • CarboxAmide(Weinreb)+Mg-R • Mg-Alkyl+CarboxAmide • Dehydration → Enone • Pd-Heck coupling • HWE → EnoateEster (intram) • Lactone-9+ • Aldol-BR2 → Aldol • O-H → O-C(O)R • Alkyl-OH → Aldehyde • Enone → Allyl-OH (asym) • O-SiMe2tBu → O-H • |
| Reagents: | Malonate • CHI3 • Hydroxide, potassium • AlH4-Li+ • MnO2 • B(OTf)R2 • Alkyl-MgX • Acetic anhydride • DBU • NEt3 • Ag2O • Me-MgBr • B(Cl)(c-Hx)2 • NEt3 • PdCl2(PPh3)2 • P(O)(OR)2CH2-C(O)OR' • BOP • DDQ • DMSO, (COCl)2 (Swern) • NEt3 • NaH • DMAP • HF·Py • Chiral catalyst (amino-alcohol) • Corey oxazaborolidine • Methacrylate • |