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Total synthesis of Poison Frog Alkaloid (-)-205B:
Reference: Smith, A. B. III; Kim, D. S. Org. Lett. 2005, 7, 3247. DOI
Keywords: N-H → N-SO2R • Li-Me+CarboxEster • CarboxEster+Li-R • Ketone → Ketal • O-H → O-SiPh2tBu • Ketal → Ketone • Amine-6 • Aldehyde → Alkyl-OH • Ketal(thio) → Ketone • CarboxEster → Ketone • B-Allyl-Ipc+Aldehyde • Aldol-B-Ipc • Mitsunobu → Aziridine • Alkyl-OH → Alkyl-NR2 • Aziridine • RCM → Ring-N • Wittig-methoxymethyl • Reductive formylation • Wittig-methyl • Alkene isomerization • Alkyl-OH → Alkyl-H • Diol-1,2 → Epoxide • CompE+-CarboxEster/Aziridine+Li-R • O-SiMe2tBu → O-H • Li-Dithiane+Epoxide • Li-Dithiane+Aziridine • N-H → N-Alkyl(2°) • Amine-6 •
Reagents: TsCl, NEt3 • PPh3, DEAD • Aziridine • MeLi • SiMe3-OTf • Aziridine • Chiral auxiliary-Boronate • BF3·OEt2 • H2O2, NaOH • SiPh2tBu-Cl • Camphor sulfonic acid • NaH • Epoxide • HCl, H2O • LiN(SiMe3)2 • Grubbs II • PPh3=CH-OMe • HCl, H2O • BH4-Na+ • Sulfonyl chloride, methane, NEt3 • BH(Et)3-Li+ • Iodosobenzene-TFA • PPh3=CH2 • TsOH • Crotyl-B(Ipc)2 • SiMe3-Cl • Imidazole • BuLi(n) • Fluoride, R4N+ • Sulfonyl chloride, methane • Na(Hg) •

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