Total synthesis of Antillatoxin Isomer:
| Reference: | Yokokawa, F.; Shioiri, T. J. Org. Chem. 1998, 63, 8638. DOI |
| Reactions: | Allyl-OH → Enal • O-H → O-SiEt3 • EnoateEster → Allyl-OH • Alkyl-OH → Aldehyde • O-SiEt3 → O-H • Selenide → Selenoxide • HWE → EnoateEster-cis • Pd/B-Vinyl+Vinyl-X • Aldol-B-Evans • CarboxAmide enolate+Aldehyde (asym) • Li-Selenide+EneLactone • EneLactone+Li-R • ConjAdd Li-R • Selenoxide-Ei → Ene • O-Allyl → O-H • Pd-Deallylation • Hydroboration Alkyne • Lactam-9+ • Lactone-6 • CarboxAmide(Evans) → CarboxAcid • CarboxAcid → CarboxEster • Williamson esterification • CarboxAcid → CarboxEster • Williamson esterification • CarboxEster → CarboxAcid • |
| Reagents: | Chiral auxiliary (amide-Evans) • B(OTf)Bu2 • Hydroxide, lithium • BH(Catechol) • Vinyl-I • Pd° • MnO2 • KH • SiEt3-Cl • AlHiBu2 • RuO4-Pr4N+, NMO • KN(SiMe3)2 • Acetic acid, trifluoro • LiCH2-SePh • Hydroxide, lithium • Allyl-Br • Periodate, sodium • Pd° • HMPA (solvent) • Chiral auxiliary (amide-Evans) • 18-crown-6 • P(O)(OCH2CF3)2CH2-C(O)OMe • |