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Total synthesis of Amphidinol 3 (Part 1):
Reference: Huckins, J. R.; Vicente, J. de; Rychnovsky, S. D. Org. Lett. 2007, 9, 4757. DOI
Keywords: B-Allyl+Aldehyde • O-H -> O-Bn • O-H -> O-SiMe2tBu • O-SiMe2tBu -> O-H • Alkyl-OH -> Aldehyde • Mg-Vinyl+Aldehyde • Allyl-OH -> Enone • O-Bn -> O-H • O-H -> O-SO2R • Diol -> Epoxide • O-H -> O-SEM • B-Allyl-Tartrate+Aldehyde • Hydroboration Alkene • Mitsunobu -> SR • Alkyl-OH -> Alkyl-SR • Julia-Kocienski • Sharpless dihydroxylation • Alkene -> Diol-1,2(asym) • Olefin cross metathesis • Epoxide+Thiol •
Reagents: Allyl-B(tartrate) • NaH • 9-BBN-H • H2O2 • PPh3, DIAD • Mo7O24(NH4)6 • H2O2 • KN(SiMe3)2 • AD-Mix • SiMe2tBu-OTf • Lutidine • Al2O3 • IBX • Vinyl-MgX • IBX • Grubbs-Hoveyda • LiDBB • MeSO2Cl • Carbonate, potassium • NEtiPr2 • NaH • HS-Ph • DMSO (solvent) •

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