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Total synthesis of Allopumiliotoxin 267A:
Reference: Comins, D. L.; Huand, S.; McArdle, C. L.; Ingalls, C. L. Org. Lett. 2001, 3, 469. DOI
Keywords: Aldol-Li → Enone • Alkyne → Alkane • Lactam-5 • O-C(O)R → O-H • CarboxAmide → Amine • Amine-5 • Felkin-Anh Chelation • Li/H → Li-Pyridyl • Ketone → Ketone-α-OR • Li-Alkynyl+Pyridinium • Pyridinium+M-R • Li/H → Li-Alkynyl • Alkyl-OH → Ketone-α-OR • Li-Aryl+Alkyl-X • Alkyl-X+Li-R • Lactam-5 • Si-Vinyl → H-Vinyl • Enone → Allyl-OH • ConjReduct Enone • N-C(O)OR → N-H •
Reagents: Mesityl-Li • MeI • H2, Pd • LiOMe • Pb(OAc)4 • Formic acid • BH(sBu3)-K+ • DMSO, (COCl)2 (Swern) • LiCPh3 • DBU • BH(OAc)3-Me4N+ • Acetic anhydride, trifluoro • AlH4-Li+ • DMAP • O=C(OR)Cl • Alkynyl-Li • Propiolate • Chiral auxiliary-Ester •

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