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Total synthesis of Laurenyne:
Reference: Overman, L. E.; Thompson, A. S. J. Am. Chem. Soc. 1988, 110, 2248. DOI
Keywords: EnoateEster → Allyl-OH • Aldehyde → Enal • Saegusa oxidation • O-H → O-SO2R • Si-Alkynyl → H-Alkynyl • HWE → EnoateEster-cis • Peterson → Enyne • Li-Allenyl/Propargyl+Aldehyde • Aldehyde+Li-R • Nitrile → Aldehyde • CompRed-Nitrile/Alkene+M-H • Li-Vinyl+Oxetane • Saegusa oxidation • Aldehyde → Enal • EnolSilane → Enal • Allyl-OR → Allyl-H • Sharpless epoxidation • O-SiPh2tBu → O-H • Si-Vinyl+Acetal • Acetal+Si-R • Ether-8 • EnolEther → Acetal • Alkyl-X → Alkyl-CN • CompE+-Alkyl-X/Alkyl-X+NaCN • Alkyl-OH → Aldehyde • Epoxide → Chlorohydrin • O-H → O-SO2R • Si-Vinyl → H-Vinyl • Alkyl-OH → Aldehyde • Aldehyde → Enol-R • Enal → Allyl-OH • Li/H → Li-Alkynyl • Epoxide+Li-R • O-H → O-SiPh2tBu • Alkyne → Ene-cis (Lindlar) •
Reagents: Oxetane • CrO3Cl·PyH (PCC) • P(O)(OCH2CF3)2CH2-CO2Me • KN(SiMe3)2 • AlHiBu2 • Hydroperoxide, tbutyl - Ti • Epoxide • Ti(OiPr)4 • TsCl, Py • Vinyl-OR • TsOH·Py • CrO3Cl·PyH (PCC) • NHiPr2 • Pd(OAc)2 • Cyanide, sodium • AlHiBu2 • AlHiBu2 • Sulfonyl chloride, methane, NEt3 • BH4-Na+ • Allenyl-Li • Fluoride, R4N+ • BuLi(sec) • HF·Py • 18-crown-6 • DMSO (solvent) • HMPA (solvent) • SnCl4 • Fluoride, R4N+ • BF3·OEt2 • HMPA (solvent) • Alkynyl-Li • NH3 • Epoxide • SiPh2tBu-Cl • H2, Pd • Epoxide •

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