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Total synthesis of Hemibrevetoxin B (Part 2):
Reference: Zakarian, A.; Batch, A.; Holton, R. A.. J. Am. Chem. Soc. 2003, 125, 7822-7823. DOI
Keywords: CarboxAcid -> Alkyl-OH • Alkyl-OH -> Aldehyde-α-OR • O-SiEt3 -> O-H • Wittig-alkyl -> Ene-cis • O-Bn -> O-H • O-SiiPr3 -> O-H • Diol-1,2 cleavage • Hydrogenation EnoateEster • O-H -> O-SiMe3 • CarboxEster -> Aldehyde • Ketal -> Ketone • O-MOM -> O-H • Alkyl-OH -> Aldehyde • RCM -> Ring-O • Ether-7 • Peterson -> Ene • HWE -> EnoateAmide • B-Allyl+Aldehyde • Peterson -> Diene • Selenoxide-Ei -> Ene • Selenoetherification • Ether-7 •
Reagents: AlH4-Li+ • DMSO, (COCl)2 • PPh3=CH-Me • HF·Py • H2O2 • Li°/NH3 • MgCH2-SiMe3 • KOtBu • Fluoride, Bu4N+ • Periodate, sodium • Weinreb phosphonate • NaH • H2, Pd • SiMe3-Cl • AlHiBu2 • Allyl-BR2 • KOtBu • Camphor sulfonic acid • SnBu2(O) • DMSO, (COCl)2 • LiBF4 • Grubbs II • Iodide, Bu4N+ • SePh-Phthalimide •

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