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Total synthesis of Elaiolide:
Reference: Paterson, I.; Lombart, H. -G.; Allerton, C. Org. Lett. 1999, 1, 19. DOI
Keywords: Ketone → EnolBorane • Ketone → Alkyl-OH • Alkene cleavage • Ketone → EnolBorane • Ketone → Alkyl-OH • Diol-1,3 → Ketal • O-Bn → O-H • Alkyl-OH → Aldehyde • Takai-Utimoto → Vinyl-I • Aldol-B • Aldol-B • Ketal → Diol-1,3 • Pd-Stannylation • Vinyl-I → Vinyl-Sn • CarboxAcid → CarboxEster • O-H → O-SiEt3 • O-PMB → O-H • Alkyl-OH → Ketone • O-SiEt3 → O-H • Aldol-Li → Aldol • Ketone enolate+Aldehyde • Felkin-Anh • Cu-Vinyl+Vinyl-X • Vinyl-X+Cu-R •
Reagents: B(Cl)(c-Hx)2 • NMe2Et • Acetaldehyde • H2O2 • Acetonitrile, trichloro • 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 • Camphor sulfonic acid • SnMe3-SnMe3 • PdCl2(PPh3)2 • Carbodiimide • SiEt3-Cl • DDQ • Dess-Martin • LiN(SiMe3)2 • HF • CuOC(O)R •

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