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Total synthesis of Halichlorine core:
Reference: Feldman, K. S.; Perkins, A. L.; Masters, K. M. J. Org. Chem. 2004, 69, 7928. DOI
Keywords: Si-Alkynyl -> H-Alkynyl • Alkyne -> Sn-Alkynyl • Sn-Alkyl -> Alkyl-Br • CarboxAmide -> Alkyl-OH • O-H -> O-SiPh2tBu • RCM -> Ring-N • B-Allyl+Pyridine • Hydrostannation Alkene • Selenoxide-Ei -> Ene • Sn-Alkyl+Enone • Enone+Sn-R • Hydrogenation Alkene • Amine+Alkyl-X • Amine+CarboxCl • Dehydrohalogenation -> Ene • Sn-Alkyl -> Alkyl-Br • Carbene insertion • Lactam-5 • CarboxAmide enolate+Alkyl-X •
Reagents: Allyl-BR2 • HSnBu3 • H2, Pt • Alkyl-SnR3 • Alkyl-SnR3 • Propiolyl-Cl • NEtiPr2 • Alkynyl-SnR3 • Fluoride, Bu4N+ • SnBu3-OSnBu3 • Iodosobenzene-cyanotriflate • Sulfinate, toluene • MgBr2 • Li°Naphth • Bromine • KOtBu • Iodosobenzene • H2O2, KHCO3 • Selenocyanate, o-nitrophenyl • MeOTf • AlH4-Li+ • Allyl-Br • SiPh2tBu-Cl • Grubbs I • AIBN • BF3

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