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Total synthesis of Hamigeran B:
Reference: Trost, B. M.; Pissot-Soldermann, C.; Chen, I.; Schroeder, G. M. J. Am. Chem. Soc. 2004, 126, 4480. DOI
Keywords: Alkyl-OH → Ketone • O-H → O-Tf • Aryl-OMe → Aryl-OH • Pd-Heck coupling • Pd-enolate allylation(asym) • Cu-Me+Enone-β-X • Enone-β-X+Cu-R • ConjAdd Cu-R • Alkene cleavage • CompE+-Aldehyde/Vinyl-X+Li-R • Hydrogenation alkene • EnolTriflate → Vinyl-H • Ketone → EnolTriflate • Ketone → Ketone-1,2-di • Aryl-H → Aryl-Br • PdCl(Allyl) •
Reagents: Trost bisphosphine • Chiral catalyst • LiNiPr2 • LiNiPr2 • Tf2NPh • LiCuMe2 • OsO4, NMO • Dess-Martin • BCl3 • Pd, formic acid • Tf2O • Pd(OAc)2 • H2, Ir • Pd/C • BBr3 • SeO2 • NBS • Periodate, sodium • Allyl-OAc •

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