Total synthesis of Leustroducsin B (Part 2):
| 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 1) |
| Reactions: | O-PMB → O-H • Staudinger • Li/I → Li-Vinyl • Li-R → Zn-R • Zn-Vinyl+Ketone • CompE+-Ketone/Azide+M-R • Acetal → EnoateEster • Lactone-6 • Diimide+Alkyne • CompRed-Alkyne/Alkene+Diimide • Pd/Si-Vinyl+Vinyl-X • O-H → O-P(O)X2 • Azide → Amine • Felkin-Anh Chelation • O-H → O-SiEt3 • CompNu-O-H/O-H+R3Si-X • N-Alloc → N-H • O-H → O-SiMe3 • N-H → N-C(O)OR • Phosphite → Phosphate • O-Allyl → O-H • Pd-Deallylation • |
| Reagents: | BuLi(tert) • CrO3Cl·PyH (PCC) • Diimide • NEt3 • Pd2(dba)3 • Fluoride, R4N+ • Acetic acid • SiEt3-OTf • SiMe3-OTf • DDQ • PPh3 • O=C(OAllyl)Cl (Alloc) • Pyridine • Lutidine • Pd(PPh3)4 • Hydroperoxide, tbutyl • Formic acid • |