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Total synthesis of Antillatoxin Isomer:
Reference: Yokokawa, F.; Shioiri, T. 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 • HWE → EnoateEster-cis • Pd/B-Vinyl+Vinyl-X • Suzuki coupling • Aldol-B-Evans • Li-Selenide+EneLactone • EneLactone+Li-R • ConjAdd Li-R • Selenoxide-Ei → Ene • N-Allyl → N-H • Hydroboration Alkyne • Lactam-9+ •
Reagents: Chiral auxiliary-Evans • BOTfBu2 • Hydroxide, lithium • BH(Catechol) • Vinyl-I • Pd° • MnO2 • MeI • SiEt3-Cl • AlHiBu2 • RuO4-Pr4N+, NMO • KN(SiMe3)2 • Acetic acid, trifluoro • LiCH2-SePh • Hydroxide, lithium • Allyl-Br • Periodate, sodium • Pd° • HMPA (solvent) • 18-cr-6 • P(O)(OCH2CF3)2CHR-CO2Me •

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