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Total synthesis of Iejimalide B (Part 1):
Reference: Schweitzer, D.; Kane, J. J.; Strand, D.; McHenry, P.; Tenniswood, M.; Helquist, P. Org. Lett. 2007, 9, 4619 ASAP DOI
Keywords: O-H -> O-SiPh2tBu • CarboxEster -> Alkyl-OH • Alkyl-OH -> Aldehyde • O-SiPh2tBu -> O-H • Sulfide -> Sulfone • Lactone -> Lactol • O-H -> O-Me • CarboxEster -> Alkyl-OH • O-SiMe2tBu -> O-H • Alkyl-OH -> Aldehyde • O-H -> O-Me • O-H -> O-Me • Allyl-OH -> Enal • CarboxEster -> CarboxAcid • O-H -> O-SiPh2tBu • EnoateEster -> Allyl-OH • Allyl-OH -> Enal • Julia-Kocienski • O-SiPh2tBu -> O-H • Sulfide -> Sulfone • Si-Vinyl -> Vinyl-I • Wittig-carboxymethyl -> EnoateEster • Wittig-carboxymethyl -> EnoateEster • Julia-Kocienski • Zn-Alkynyl(asym)+Aldehyde • Aldehyde+Zn-R • Wittig-alkyl+Ketone • Mitsunobu -> SR • Alkyl-OH -> Alkyl-SR • Mitsunobu -> SR • Alkyl-OH -> Alkyl-SR •
Reagents: SiPh2tBu-Cl • AlHiBu2 • DMSO, (COCl)2 • PPh3=C(Me)-CO2R • Fluoride, ammonium • PPh3 • DEAD • H2O2 • H2SO4 • Chloral • AlHiBu2 • MeI • BH3·SMe2 • PPh3=C(Me)-CO2R • TsOH·Py • DMSO, Py·SO3 • Zn(OTf)2 • Me2SO4 • Hydroxide, sodium • ZrCp2ClH • Fluoride, Bu4N+ • RuO4-Pr4N+, NMO • LiN(SiMe3)2 • Hydroxide, lithium • SiPh2tBu-Cl • AlHiBu2 • MnO2 • LiN(SiMe3)2 • Fluoride, ammonium • PPh3 • DEAD • H2O2 • NEt3 • Alkynyl-SiR3 • NEt3 • NIS • Imidazole •

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