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Total synthesis of Xanthatin, Dihydro:
Reference: Evans, M. A.; Morken, J. P. Org. Lett. 2005, 7, 3371. DOI
Keywords: O-H -> O-SiMe2tBu • Pinnick oxidation • Aldehyde -> CarboxAcid • CarboxAcid -> CarboxEster • Enone -> Allyl-OH(asym) • Alkyl-OH -> Aldehyde • O-SiMe2tBu -> O-H • Alkyl-OH -> Aldehyde • Jones oxidation • Lactol -> Lactone • Lactone-5 • HWE -> Enone • Li-Phosphonate+CarboxEster • Oxazaborolidine BH3 • Ketone -> Alkyl-OH(asym) • Wittig-methyl • Seyferth-Gilbert homologation • Aldehyde -> Alkyne • Enyne metathesis • Olefin cross metathesis • Hydroboration Alkene • Nitrile -> Aldehyde • Alkyl-X -> Alkyl-CN • Lactone enolate+Alkyl-X • Pd-Heck coupling •
Reagents: Cyanide, sodium • SiMe2tBu-Cl • AlHiBu2 • Chlorite, sodium • Diazomethane, silyl • P(O)(OR)2CH2-C(O)R • Bromide, lithium • Corey oxazaborolidine • BH3·SMe2 • Cu(OAc)2 • BH-BBN • Dess-Martin • PPh3=CH2 • Fluoride, Bu4N+ • Dess-Martin • CrO3, H2SO4 (Jones) • LiNiPr2 • MeI • Grubbs II • Methyl vinyl ketone • Grubbs II • Vinyl-OR • Diazophosphonate • H2O2, NaOH • Acetaldehyde • Pd(OAc)2

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