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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 (Part 2)
Keywords: 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-1,2 → Epoxide • O-H → O-SEM • B-Allyl-Tartrate+Aldehyde • Aldol-B-Tartrate • Hydroboration Alkene • Mitsunobu → SR • Alkyl-OH → Alkyl-SR • Julia-Kocienski • Sharpless dihydroxylation • Alkene → Diol-1,2(asym) • Olefin cross metathesis • Epoxide+Thiol • O-H → O-Bn •
Reagents: Allyl-B(tartrate) • Chiral auxiliary-Boronate • NaH • BH-BBN • H2O2, NaOH • PPh3, DIAD • Mo7O24(NH4)6 • H2O2, Mo • KN(SiMe3)2 • AD-Mix • SiMe2tBu-OTf • Lutidine • Al2O3 • IBX • Vinyl-MgX • IBX • Grubbs-Hoveyda • LiDBB • Sulfonyl chloride, methane • Carbonate, potassium • NEtiPr2 • NaH • Thiol, phenyl • DMSO (solvent) • Citric acid • Benzyl-X •

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