Total synthesis of Elaiolide:
| Reference: | Paterson, I.; Lombart, H. -G.; Allerton, C. Org. Lett. 1999, 1, 19. DOI |
| Reactions: | Ketone → EnolBorane • O-Bn → O-H • CompRed-O-Bn/O-PNB+H2 • Aldol-BR2 → Aldol • Aldol-BR2 → Aldol • Ketal → Diol-1,3 • Pd-Stannylation • Vinyl-I → Vinyl-Sn • O-SiEt3 → O-H • Aldol-Li → Aldol • Ketone enolate+Aldehyde • Felkin-Anh • Cu-Vinyl+Vinyl-X • Vinyl-X+Cu-R • O-H → O-PMB • Ketone → Alkyl-OH • Felkin-Anh Chelation • Takai-Utimoto → Vinyl-I • Lactone-9+ • O-PMB → O-H • Alkyl-OH → Ketone • O-H → O-SiEt3 • Alkyl-OH → Aldehyde • Diol-1,3 → Ketal • Ketone → Alkyl-OH • Diol-1,2 cleavage • CarboxAcid → CarboxEster • CompNu-O-H/O-H+RC(O)X • O-C(O)R → O-H • Ketone → EnolBorane • |
| Reagents: | B(Cl)(c-Hx)2 • NMe2Et • Acetaldehyde • H2O2 • PMBO-C(=NH)-CCl3 • BH4-Na+ • Periodate, sodium • B(Cl)(c-Hx)2 • NEt3 • H2O2 • BH(OAc)3-Me4N+ • Me2C(OMe)2 • TsOH·Py • H2, RaNi • DMSO, (COCl)2 (Swern) • CHI3 • Vinyl-I • Sulfonic acid, Camphor • SnMe3-SnMe3 • PdCl2(PPh3)2 • Acrylate • Vinyl-I • Carbodiimide • SiEt3-Cl • DDQ • Dess-Martin • LiN(SiMe3)2 • HF • CuOC(O)R • Carbonate, potassium • |