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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 -> Ketal • O-Bn -> O-H • Alkyl-OH -> Aldehyde • Takai-Utimoto -> Vinyl-I • Aldol-B • Aldol-B • Ketal -> Diol • Pd-Stannylation • Vinyl-I -> Sn-Vinyl • 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: BCl(c-Hx)2 • NMe2Et • Acetaldehyde • H2O2 • Acetonitrile, trichloro • BH4-Na+ • Periodate, sodium • BCl(c-Hx)2 • NEt3 • H2O2 • BH(OAc)3-Me4N+ • Me2C(OMe)2 • TsOH·Py • H2, RaNi • DMSO, (COCl)2 • 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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