Total synthesis of O-Methyl-Myxalamide D:
| Reference: | Coleman, R. S.; Lu, X.; Modolo, I. J. Am. Chem. Soc 2007, 129, 3826. DOI |
| Reactions: | CompRed-Alkyne/Alkene+M-H • O-SiMe2tBu → O-H • Pd/Zn-Allenyl/Propargyl+Aldehyde • Takai-Utimoto → B-Vinyl • Pd/B-Vinyl+Vinyl-X • Pd/Sn-Vinyl+Vinyl-X • Alkyne Hydrostannation • Cu-SnR3+Alkyne • Epoxide+Na-Alkynyl • Mechanism • Alkyne Hydrozirconation • CompNu-Sn-Vinyl/B-Vinyl+R-I • Zr-Vinyl → X-Vinyl • O-H → O-SiMe2tBu • Allyl-OH → Enal • O-H → O-SO2Me • |
| Reagents: | Sulfonyl chloride, methane, NEt3 • Crotonaldehyde • ZnEt2 • Pd(OAc)2 • Vinyl-Zr • I2 • SiMe2tBu-OTf • Fluoride, R4N+ • Epoxide • Alkynyl-Na • NH3 • CuCN • DMSO, Py·SO3 (Parikh-Doering) • Alkyl-BR2 • CrCl2 • PdCl2(dppf) • AsPh3 • Vinyl-BR2 • AsPh3 • Pd2(dba)3 • Vinyl-I • Vinyl-I • |