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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: CarboxAcid → CarboxEster • CarboxEster → Alkyl-OH • O-H → O-SiMe2tBu • Allyl-OH → Enone • N-Boc → N-H • O-SiMe2tBu → O-H • Si-Alkyl → HO-Alkyl • HWE → EnoateEster • Selenoxide-Ei → EneLactam • Lactam → EneLactam • Sharpless epoxidation • CarboxAmide → CarboxAmide-α-SeR • Lactam-5 • Li-SiR3+EnoateAmide • ConjAdd-Aldol • EnoateEster → Allyl-OH • Alkyl-OH → Aldehyde-α-OR • EnoateEster → Allyl-OH • Alkyl-OH → Aldehyde • HWE → EnoateEster • Enone → Enone-α-OR •
Reagents: SOCl2 • BH4-Na+ • SiMe2tBu-Cl • Boc2O • LiNiPr2 • H2O2 • P(O)(OR)2CH2-CO2R • Dess-Martin • Dioxirane • Perbenzoic acid, 3-chloro • Acetic acid, trifluoro • H2SiF6 • SePh-Br • Ni(acac)2 • DMAP • Bifluoride, potassium • LiSiR3 • AlHiBu2 • Dess-Martin • P(O)(OR)2CH2-CO2R • AlHiBu2 • Dess-Martin • Dess-Martin •

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