Total synthesis of Leustroducsin B (Part 1):
| Reference: | Trost, B. M.; Biannic, B.; Brindle, C. S.; O'Keefe, B. M.; Hunter, T. J.; Ngai, M.-Y. J. Am. Chem. Soc. 2015, 137, 11594-11597. DOI (Part 2) |
| Reactions: | CompRed-CarboxAmide/Alkyne+M-H • CompRed-Alkyne/Alkene+M-H • O-H → O-SiMe2tBu • Hydrogenation Alkene • Aldol-B-Evans • CarboxAmide enolate+Aldehyde (asym) • CarboxAmide(Evans) → Aldehyde • Wittig-alkyl → Ene-cis • Claisen acylation, formate • CarboxEster enolate+CarboxEster • Wittig-methyl • CompE+-Aldehyde/CarboxEster+Wittig • Aldol-Zn (asym) • Ketone → Alkyl-OH (asym) • ConjAdd M-N3 • Enone+Azide • Pd-allyl-O coupling • Wittig-iodomethyl • O-Bn → O-H • CarboxAcid → CarboxEster • Hydrozirconation Alkyne • O-H → O-BOM • Ketal → Ketone • Lactone → CarboxEster • O-H → O-C(O)R • Si-Alkynyl → H-Alkynyl • Acetal → Acetal • Zr-Vinyl → X-Vinyl • CarboxEster → Alkyl-OH • Alkyl-OH → Aldehyde • CarboxEster → Aldehyde • |
| Reagents: | Propiolaldehyde • Alkynyl-SiR3 • B(OTf)Bu2 • NEt3 • PPh3 • TsOH • Carbonate, potassium • ZrCp2ClH • I2 • LiNiPr2 • Formate, methyl • Carbonate, potassium • PPh3=CH2 • NaOtBu • AlHiBu2 • Alkynyl-SiR3 • Chiral catalyst (diol) • ZnEt2 • Noyori catalyst • SiMe2tBu-Cl • Imidazole • NEtiPr2 • Acetic acid • Azide, sodium • KOtBu • O=C(OMe)Cl • PdCl(Allyl) • H2, Pd • BH3·SMe2 • Dess-Martin • PPh3=CH-I • NaN(SiMe3)2 • Chiral auxiliary (amide-Evans) • Chiral catalyst (diamine) • HOMe (react) • Chiral catalyst (phosphine) • |