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Total synthesis of Pramanicin:
Reference: Barrett, A. G. M.; Head, J.; Smith, M. L.; Stock, N. S.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1999, 64, 6005. DOI
Keywords: Lactam-5 • O-H -> O-SiMe2tBu • HWE -> EnoateEster • EnoateEster -> Allyl-OH • Alkyl-OH -> Aldehyde-α-OR • EnoateEster -> Allyl-OH • Allyl-OH -> Enal • Allyl-OH -> Enone • N-Boc -> N-H • O-SiMe2tBu -> O-H • C-Si -> C-OH, Alkyl • HWE -> EnoateEster • Selenoxide-Ei -> EneLactam • Lactam -> EneLactam • Sharpless epoxidation • CarboxAmide -> CarboxAmide-α-SePh • Lactam-5 • Li-SiR3+EnoateAmide • ConjAdd-Aldol •
Reagents: SOCl2 • BH4-Na+ • SiMe2tBu-Cl • Boc2O • LiNiPr2 • H2O2 • P(O)(OR)2CH2-CO2R • AlHiBu2 • Dess-Martin • P(O)(OR)2CH2-CO2R • AlHiBu2 • Dess-Martin • Dess-Martin • Dioxirane • Perbenzoic acid, 3-chloro • Acetic acid, trifluoro • H2SiF6 • SePh-Br • Ni(acac)2 • DMAP • Bifluoride, potassium • LiSiR3

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