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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 DOI (Part 2)
Keywords: O-H → O-SiPh2tBu • O-SiPh2tBu → O-H • O-SiMe2tBu → O-H • Alkyl-OH → Aldehyde • O-H → O-Me • CompRed-Alkyne/Alkene+M-H • Allyl-OH → Enal • CarboxEster → CarboxAcid • O-H → O-SiPh2tBu • Julia-Kocienski • Li-Sulfone+Aldehyde • O-SiPh2tBu → O-H • Zr-Vinyl → X-Vinyl • Wittig-carboxymethyl → EnoateEster • Wittig-carboxymethyl → EnoateEster • Julia-Kocienski • Zn-Alkynyl+Aldehyde(asym) • Aldehyde+Zn-R • Wittig-alkyl+Ketone • Mitsunobu → SR • Alkyl-X → Alkyl-SR • Mitsunobu → SR • Alkyl-X → Alkyl-SR • Sulfide → Sulfone • Sulfide → Sulfone • Mitsunobu → SR • Alkyl-X → Alkyl-SR • O-H → O-Me • EnoateEster → Allyl-OH • CarboxEster → Alkyl-OH • Alkyl-OH → Aldehyde • CarboxAcid → Alkyl-OH • CompRed-CarboxAcid/CarboxEster+M-H • O-H → O-Me • Lactone → Lactol • CompRed-CarboxAcid/CarboxEster+M-H • Allyl-OH → Enal •
Reagents: SiPh2tBu-Cl • AlHiBu2 • DMSO, (COCl)2 (Swern) • PPh3=C(Me)-CO2R • Fluoride, ammonium • PPh3, DEAD • H2SO4 • Chloral • AlHiBu2 • Ag2O • BH3·SMe2 • PPh3=C(Me)-CO2R • TsOH·Py • DMSO, Py·SO3 (Parikh-Doering) • Zn(OTf)2 • Ephedrine • Chiral catalyst • Sulfate, dimethyl • Hydroxide, sodium • Vinyl-Zr • Fluoride, R4N+ • RuO4-Pr4N+, NMO • LiN(SiMe3)2 • Hydroxide, lithium • SiPh2tBu-Cl • AlHiBu2 • MnO2 • LiN(SiMe3)2 • Fluoride, ammonium • PPh3, DEAD • Mo7O24(NH4)6 • NEt3 • Alkynyl-SiR3 • NEt3 • NIS • Imidazole • H2O2 • H2O2, Mo •

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