Reaction scheme for total synthesis of the natural product Hemibrevetoxin B (Part 1)

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 • Lactone-6 • CarboxEster enolate+Alkyl-X • Alkyl-X+Enolate • Alkyl-OH → Alkyl-I • Epoxidation, peracid • Lemieux-Johnson oxidation • Lactone-6 • 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 • Epoxidation •
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) •