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Total synthesis of ACRL Toxin IIIb:
Reference: Munchhof, M. J.; Heathcock, C. H. J. Org. Chem. 1994, 59, 7566. DOI
Keywords: CarboxAmide(Evans) → CarboxEster • CarboxEster → Alkyl-OH • O-H → O-CPh3 • Luche reduction • Enone → Allyl-OH • Sulfide → Sulfoxide • O-H → O-SiMe2tBu • Alkyl-OH → Aldehyde • Alkyl-OH → Ketone • O-THP → O-H • Ketone → Alkyl-OH • CarboxAcid → CarboxEster • O-SiMe2tBu → O-H • CarboxAmide(Weinreb)+Li-R • Li-Vinyl+CarboxAmide • Aldol-B-Evans • 2,3-Sigmatropic Sulfoxide • Lactone enolate+Aldehyde • Aldol-Li → Aldol • Lactone-6 • CarboxAcid → CarboxAmide(Weinreb) • CarboxAmide(Evans) → CarboxEster • Claisen-Ireland •
Reagents: LiOCH2Ph • AlHiBu2 • Ph3CCl • O=C(Imid)2 • Vinyl-Li • BH4-Na+, CeCl3 • Perbenzoic acid, 3-chloro • P(OMe)3 • SiMe2tBu-OTf • ZnBr2 • DMSO, Py·SO3 (Parikh-Doering) • Dess-Martin • Acetic acid • BH(sBu3)-Li+ • Diazomethane • HF·Py • DMAP • NMe(OMe)-H • LiNiPr2 • SiMe2tBu-Cl •

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