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Total synthesis of Hemibrevetoxin B (Part 1):
Reference: Zakarian, A.; Batch, A.; Holton, R. A.. J. Am. Chem. Soc. 2003, 125, 7822-7823. DOI (Part 2)
Keywords: Alkene cleavage • Aldehyde → Alkyl-OH • CarboxEster → CarboxAcid • Henbest • Diol-1,3 → Acetal • EnoateEster → Allyl-OH • Epoxide reduction • Hydroboration alkene • Diol-1,3 → Acetal • O-H → O-MOM • Acetal → Diol • O-Bn → O-H • O-H → O-Tf • CarboxEster → CarboxAcid • O-H → O-SiiPr3 • CarboxEster → CarboxAcid • Iodolactonization • CarboxEster enolate+Alkyl-X • Alkyl-X+Enolate • Alkyl-OH → Alkyl-I • Epoxidation, peracid • Lemieux-Johnson oxidation • Furst-Plattner diaxial • Sn-Allyl+Allyl-X • Allyl-X+Sn-R • Pd/Zn-Alkyl+Vinyl-X • Negishi coupling • Alkyne Silyl-metalation • Si-Vinyl → I-Vinyl • Li-Alkynyl+Alkyl-X • Li/H → Li-Alkynyl • Alkyl-X+Li-R •
Reagents: SnBu2(O) • NaH • Camphor sulfonic acid • LiNiPr2 • OsO4, NaIO4 • BH3CN-Na+ • PPh3, I2 • Allyl-SnR3 • BF3·OEt2 • NaOMe • Perbenzoic acid, 3-chloro • Camphor sulfonic acid • AlHiBu2 • AlH4-Li+ • BH3·SMe2 • Camphor sulfonic acid • Cl-CH2-OR • Li°/NH3 • Tf2O • CuCN • NIS • Hydroxide, lithium • NIS • SiiPr3-OTf • NaOMe • Allyl-I • Lutidine • Bromoacetate • Allyl-SnR3 • BF3·OEt2 • Zn° • PdCl2(dppf) • Alkynyl-Li • DMPU (solvent) •

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