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Total synthesis of Antillatoxin Isomer:
Reference: Yomakawa, Shiori J. Org. Chem. 1998, 63, 8638. DOI
Keywords: CarboxAmide(Evans) -> CarboxAcid • Allyl-OH -> Enal • Williamson esterification • O-H -> O-SiEt3 • EnoateEster -> Allyl-OH • Alkyl-OH -> Aldehyde • O-SiEt3 -> O-H • Lactam-15+ • HWE -> EnoateEster-cis • Pd/B-Vinyl+Vinyl-X • Suzuki coupling • Aldol-B-Evans • Li-Selenide+EneLactone • ConjAdd Li-R • Selenoxide-Ei -> Ene • Li-Selenide+EnoateEster • N-Allyl -> N-H • Hydroboration Alkyne • Macrolactamization • Lactam-15+ •
Reagents: Bu2BOTf • Hydroxide, lithium • BH(Catechol) • Pd° • MnO2 • MeI • HSiEt3 • AlHiBu2 • RuO4-Pr4N+, NMO • P(O)(OCH2CF3)2CH2-CO2Me • KN(SiMe3)2 • Acetic acid, trifluoro • LiCH2-SePh • Hydroxide, lithium • Allyl-Br • Periodate, sodium • Pd° • HMPA (solvent) • 18-cr-6 •

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