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) |
| Reactions: | O-H → O-SiPh2tBu • O-SiPh2tBu → O-H • Sulfide → Sulfone • Diol-1,2 → Acetal • O-SiMe2tBu → O-H • CompE+-Si-O/Si-O+H2O • Alkyl-OH → Aldehyde • O-H → O-Me • CompRed-Alkyne/Alkene+M-H • Allyl-OH → Enal • 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 • 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 • CarboxEster → CarboxAcid • |
| Reagents: | SiPh2tBu-Cl • AlHiBu2 • DMSO, (COCl)2 (Swern) • PPh3=C(Me)-CO2R • Fluoride, ammonium • PPh3, DEAD • Thiol, benzothiazole • H2O2, Mo • H2SO4 • Chloral • AlHiBu2 • MeI • BH3·SMe2 • PPh3=C(Me)-CO2R • PPh3=CH-Alkyl • TsOH·Py • DMSO, Py·SO3 (Parikh-Doering) • Zn(OTf)2 • Ephedrine • Chiral catalyst (amino-alcohol) • Sulfate, dimethyl • Hydroxide, sodium • Vinyl-Zr • Fluoride, R4N+ • RuO4-Pr4N+, NMO • Vinyl-I • LiN(SiMe3)2 • Hydroxide, lithium • SiPh2tBu-Cl • AlHiBu2 • MnO2 • LiN(SiMe3)2 • Fluoride, ammonium • PPh3, DEAD • Thiol, benzothiazole • H2O2, Mo • NEt3 • Alkynyl-SiR3 • NEt3 • NIS • Imidazole • Ag2O • |