Total synthesis of Bipinnatin J:
| Reference: | Roethle, P. A.; Trauner, D. Org. Lett. 2006, 8, 345 DOI |
| Reactions: | Al-Vinyl → I-Vinyl • Alkyne Carboalumination • Li-Alkynyl+Aldehyde • Li/H → Li-Alkynyl • Enyne reaction • Lactone-5 • Wittig-ketomethyl → Enal • CompE+-Aldehyde/Lactone+M-R • Pd/Sn-Aryl+Vinyl-X • Nozaki-Hiyama coupling • Cr-Allyl+Aldehyde • Aldehyde+Cr-R • Enal → Allyl-OH • CompRed-Aldehyde/Lactone+M-H • Protecting group - Aldehyde • Allyl-OH → Allyl-Br • Li/H → Li-Furyl • Li-R → Sn-R • Alkyl-OH → Aldehyde • |
| Reagents: | AlMe3 • Vinyl-Al • I2 • Vinyl-I • Dess-Martin • Propiolate • LiNiPr2 • RuCp(NCMe)3PF6 • Sulfonic acid, Camphor • PPh3=C(Me)-C(O)R • BH4-Na+ • Pd(PPh3)4 • CuI • Fluoride, cesium • NBS • CrCl2 • NiCl2 • Alkynyl-Li • LiN(OMe)Me • BuLi(n) • SnMe3-Cl • |