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Total synthesis of Indolizidine 223AB:
Reference: Smith, A. B. III; Kim, D.-S. Org. Lett. 2004, 6, 1493. DOI
Keywords: O-H → O-SiMe2tBu • Hydrogenation Alkyne • Jacobson kinetic resolution • O-H → O-SO2R • Ketal(thio) → CH2 • Hydrogenolysis C-S • Zn-Alkynyl(asym)+Aldehyde • Aldehyde+Zn-R • N-SO2R → N-H • CompOx-Alkene/Alkyne+Peracid • Epoxidation, peracid • N-H → N-Alkyl • Amine-5 • Amine-6 • O-SiMe2tBu → O-H • Li-Dithiane+Epoxide • Li-Dithiane+Aziridine •
Reagents: Zn(OTf)2 • Alkynyl-ZnX • SiMe2tBu-OTf • Perbenzoic acid, 3-chloro • H2, Pd • Sulfonyl chloride, methane, NEt3 • Carbonate, potassium • H2, RaNi • Na(Hg) • Epoxide • Aziridine • Fluoride, R4N+

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