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Total synthesis of Pironetin:
Reference: Dias, L. C.; Oliveira, L. G.; Sousa, M. A. Org. Lett. 2003, 5, 265. DOI
Keywords: CarboxAmide(Evans) -> CarboxAmide(Weinreb) • O-H -> O-SiMe2tBu • CarboxAmide(Evans) -> Alkyl-OH • O-H -> O-SO2R • O-H -> O-Me • O-PMB -> O-H • Alkyl-OH -> Aldehyde • O-H -> O-SiMe2tBu • CarboxAmide(Evans) -> Alkyl-OH • Alkyl-OH -> Aldehyde • O-SiMe2tBu -> O-H • Lactone-6 • CarboxAmide(Weinreb) -> Aldehyde • Aldol-B-Evans • HWE -> EnoateEster-cis • Alkyne -> Ene-trans • Aldol-B-Evans • Li-Alkynyl+Alkyl-X • Li/H -> Li-Alkynyl • Aldol-B-Evans • Chiral auxiliary •
Reagents: NMe(OMe)-AlMe2 • SiMe2tBu-OTf • AlHiBu2 • BH4-Li+ • TsCl, NEt3 • Me3O+ X- • Alkynyl-Li • BuLi(n) • Na°/NH3 • DMSO, (COCl)2 • SiMe2tBu-OTf • BH4-Li+ • RuO4-Pr4N+, NMO • NaH • HCl • MeI • DMSO (solvent) •

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