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 |
| Reactions: | Pd-Heck coupling • Cyclohexanone • Bicyclo(430) • Pd-enolate allylation (asym) • Cu-Me+Enone-β-X • Enone-β-X+Cu-R • ConjAdd Cu-Me • Hydrogenation alkene • EnolTriflate → Vinyl-H • Ketone → EnolTriflate • Ketone → Ketone-1,2-di • Aryl-H → Aryl-Br • Alkene cleavage • Aldehyde+Li-Aryl • CompE+-Aldehyde/Vinyl-X+M-R • Alkyl-OH → Ketone • O-Me → O-H (phenol) • O-H → O-Tf (phenol) • Alkene → Diol-1,2 • O-Me → O-H (phenol) • |
| Reagents: | Trost bisphosphine • Chiral catalyst (phosphine) • LiNiPr2 • LiNiPr2 • Tf2NPh • Me-Cuprate • OsO4, NMO • Aryl-Li • Dess-Martin • B(Cl)3 • Pd, formic acid • Tf2O • Pd(OAc)2 • H2, Ir • B(Br)3 • SeO2 • NBS • Periodate, sodium • Allyl-OAc • PdCl(Allyl) • |