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Total synthesis of Neosymbioimine:
Reference: Varseev, G. N.; Maier, M. E. Org, Lett. 2007, 106, 1461 DOI
Keywords: O-H → O-SiMe2tBu • Ozonolysis • O-H → O-SiMe2tBu • O-SiMe2tBu → O-H • Alkyl-OH → Aldehyde • CarboxEster → Alkyl-OH • O-H → O-SO2R • Alkyl-X → Alkyl-CN • O-SiMe2tBu → O-H • Alkyl-OH → Ketone • Ketone → Ketal • Nitrile → Amine • Amine → Imine • Amine-6 • Aldehyde → Aldehyde-α-OH • HWE → EnoateEster • O-NR2 → O-H • N-OR → N-H • Wittig-ketomethyl → Enal • HWE → Styrene • Diels-Alder, Intram • Li-Nitrile+Alkyl-X • Alkyl-X+Enolate • ArylO-Me → ArylO-H • ArylO-H → ArylO-SO3H •
Reagents: SiMe2tBu-Cl • O3 • Nitrosobenzene • Proline • P(O)(OR)2CH2-CO2R • DBU • Cu(OAc)2 • SiMe2tBu-Cl • Camphor sulfonic acid • Dess-Martin • PPh3=C(Me)-C(O)R • P(O)(OR)2CH2-Ar • KOtBu • AlHiBu2 • Sulfonyl chloride, methane, NEt3 • Cyanide, sodium • LiNiPr2 • Fluoride, R4N+ • Dess-Martin • Camphor sulfonic acid • AlH4-Li+ • HCl, H2O • B(Br)3 • SO3·Py • DMSO (solvent) •

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