Total synthesis of Poison Frog Alkaloid (-)-205B:
| Reference: | Smith, A. B. III; Kim, D. S. Org. Lett. 2005, 7, 3247. DOI |
| Reactions: | N-H → N-SO2R • Alkyl-X → Alkyl-H • CarboxEster+Li-R → Ketone • Li-Me+CarboxEster • B-Allyl-Ipc+Aldehyde • Aldehyde+B-Allyl (asym) • Mitsunobu → Aziridine • Alkyl-OH → Alkyl-NR2 • Aziridine • RCM → Ring-N • Amine-6 • Bicyclo(440)-aza • Bicyclo(430)-aza • Wittig-methoxymethyl • Reductive formylation • Wittig-methyl • Alkene isomerization • Alkyl-OH → Alkyl-H • Aldehyde → CH3 • Diol-1,2 → Epoxide • CompE+-CarboxEster/Aziridine+M-R • O-SiMe2tBu → O-H • O-H → O-SO2Me • N-SO2R → N-H • Li-Dithiane+Epoxide • Brook rearrangement • Li-Dithiane+Aziridine • N-H → N-Alkyl (2°) • Amine-6 • Amine-5 • Bicyclo(430)-aza • O-H → O-SiPh2tBu • CompE+-Si-O/Si-O+H2O • Ketone → Ketal • Ketal → Ketone • Ketone → EnolSilane • O-SiMe2tBu → O-H • Ketal(thio) → Ketone • Aldehyde → Alkyl-OH • O-H → O-SO2Me • |
| Reagents: | TsCl, NEt3 • PPh3, DEAD • Aziridine • Me-Li • SiMe3-OTf • Aziridine • Glycol, bistrimethylsilylether • Chiral auxiliary (boronate) • BF3·OEt2 • H2O2, NaOH • SiPh2tBu-Cl • Sulfonic acid, Camphor • NaH • Epoxide • HCl, H2O • LiN(SiMe3)2 • Grubbs II • PPh3=CH-OR • 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) • |