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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)
Keywords: EnoateEster → Allyl-OH • Allyl-OH → Enal • CarboxEster → Carboxamide • Abiko-Masamune Aldol • Aldol-B • O-H → O-Alkyl • O-PMB → O-H • Alkyl-OH → Aldehyde • Enone → Allyl-OH(asym) • O-SiMe2tBu → O-H • Carbene • CarboxEster enolate+Alkyl-X • Alkyl-X+Enolate • CarboxAmide(Weinreb)+Mg-R • Mg-Alkyl+CarboxAmide • Dehydration → Enone • Pd-Heck coupling • HWE → EnoateEster • Aldol-B •
Reagents: CHI3 • Hydroxide, potassium • AlH4-Li+ • MnO2 • B(OTf)(c-Hx)2 • Alkyl-MgX • Acetic anhydride • DBU • NEt3 • Ag2O • MeMgBr • B(Cl)(c-Hx)2 • NEt3 • PdCl2(PPh3)2 • BOP • DDQ • DMSO, (COCl)2 (Swern) • NEt3 • NaH • DMAP • Corey oxazaborolidine • HF·Py •

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