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Total synthesis of Laurenyne:
Reference: Overman, L. E.; Thompson, A. S. J. Am. Chem. Soc. 1988, 110, 2248. DOI
Keywords: Alkyl-OH -> Aldehyde • EnoateEster -> Allyl-OH • Epoxide -> Chlorohydrin • O-H -> O-SO2R • Alkyl-OH -> Aldehyde • Aldehyde -> Enolsilane • Aldehyde -> Enal • Saegusa oxidation • Alkyl-X -> Alkyl-CN • CompE+-Alkyl-X/Alkyl-X+NaCN • Enal -> Allyl-OH • O-H -> O-SO2R • Si-Alkynyl -> H-Alkynyl • HWE -> EnoateEster-cis • Peterson -> Enyne • Li-Allenyl/Propargyl+Aldehyde • Aldehyde+Li-R • Nitrile -> Aldehyde • Li-Vinyl+Oxetane • Si-Vinyl -> H-Vinyl • Saegusa oxidation • Aldehyde -> Enal • Enolsilane -> Enal • Allyl-OR -> Allyl-H • Sharpless epoxidation • O-SiPh2tBu -> O-H • Si-Vinyl+Acetal • Ether-8 •
Reagents: BF3·OEt2 • CrO3Cl·PyH (PCC) • P(O)(OCH2CF3)2CH2-CO2Me • KN(SiMe3)2 • AlHiBu2 • Epoxide • Ti(OiPr)4 • TsCl, Py • Vinyl-OR • TsOH·Py • CrO3Cl·PyH (PCC) • NHiPr2 • Pd(OAc)2 • Cyanide, sodium • AlHiBu2 • AlHiBu2 • MeSO2Cl, NEt3 • BH4-Na+ • Allenyl-Li • Fluoride, Bu4N+ • BuLi(sec) • HF·Py • 18-cr-6 • DMSO (solvent) • HMPA (solvent) • SnCl4 • Fluoride, Bu4N+ • HF·Py •

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