Total synthesis of Pupukeanone, 9-Isocyano- (Yamamoto):
| Reference: | Yamamoto, H.; Sham, H. L. J. Am. Chem. Soc. 1979, 101, 1609. DOI |
| Reactions: | Enone → Allyl-OH • O-THP → O-H • Corey-Kim • Alkyl-OH → Ketone • Imine → Amine • Claisen-EnolEther • Allylic oxidation → Enone • CompOx-Alkene/Alkene+CrO3 • Mg-Vinyl+Aldehyde • Hydrogenation Diene • Li-Vinyl+Ketone • N-C(O)H → N=C • Amine → Isocyanide • Enone → EnolSilane • Dehydration → Diene • Oxime → Amine • Diels-Alder, Intram, Ene • Bicyclo(321) • O-H → O-THP • Ketone → Ketal • Ketal → Ketone • Ketone → Oxime • N-H → N-C(O)H • Reductive amination, Al-H • |
| Reagents: | AlHiBu2 • Vinyl-OR • Vinyl-MgX • CrO3·Py2 (Collins) • LiNiPr2 • SiMe3-Cl • Acetic acid • Glycol • Me2S·Cl2 • Propenyl-Li • Sulfonyl chloride, methane, NEt3 • H2, Ir • NH2OH • TiCl3 • Acetic acid • AlHiBu2 • TsCl, Py • Hg(OAc)2 • Butadiene, 2-OR • DHP • Formic acetic anhydride • |