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Total synthesis of 9-Isocyano-Pupukeanone:
Reference: Yamamoto, H.; Sham, H. L. J. Am. Chem. Soc. 1979, 101, 1609. DOI
Keywords: Enone → Allyl-OH • O-H → O-THP • O-THP → O-H • Ketone → Ketal • Corey-Kim • Ketone → Oxime • Ketal → Ketone • Imine → Amine • Claisen-Enol ether • Allylic oxidation → Enone • Mg-Vinyl+Aldehyde • Hydrogenation Diene • Li-Vinyl+Ketone • Reductive amination, Al-H • Amine → Isocyanide • Enone → EnolSilane • Dehydration → Ene • Oxime → Amine • Diels-Alder, Intram •
Reagents: AlHiBu2 • Vinyl-OR • Vinyl-MgX • DHP • CrO3·Py2 (Collins) • LiNiPr2 • SiMe3-Cl • Acetic acid • Glycol • Me2S·Cl2 • Propenyl-Li • Sulfonyl chloride, methane, NEt3 • H2, Ir • NH2OH • TiCl3 • Acetic acid • AlHiBu2 • Formic acetic anhydride • TsCl, Py • Hg(OAc)2 • AlHiBu2

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