| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348175 | Tetrahedron: Asymmetry | 2008 | 4 Pages |
A short efficient enantioselective synthesis leading directly to (+)-(S)-kurasoin B has been achieved in 5 steps and 25% overall yield from (2E)-ethyl-4-phenylbut-2-enoate using Sharpless asymmetric dihydroxylation and CH3NO2-assisted, or Yb(OTf)3-catalyzed, regioselective C-3 coupling of indole as the key steps.
Graphical abstractAn efficient short enantioselective synthesis leading directly to (+)-(S)-kurasoin B has been achieved in 5 steps and 25% overall yield from (2E)-ethyl-4-phenylbut-2-enoate using Sharpless asymmetric dihydroxylation and CH3NO2-assisted or Yb(OTf)3-catalyzed regioselective C-3 coupling of indole as the key steps.Figure optionsDownload full-size imageDownload as PowerPoint slide
(+)-(2S,3S)-1,2-Epoxy-4-phenylbutan-3-olC10H12O2Ee = 95%[α]D20=+6.42 (c 1.8, CHCl3)Source of chirality: asymmetric dihydroxylationAbsolute configuration: (2S,3S)
(−)-(2S)-1,2-Epoxy-4-phenylbutan-3-oneC10H10O2Ee = 95%[α]D20=-36.4 (c 1.5, CHCl3)Source of chirality: enantiopure reactantAbsolute configuration: (2S)
(+)-(S)-3-Hydroxy-4-(1H-indol-3-yl)-1-phenylbutan-2-oneC18H17NO2Ee = 95%[α]D20=+30.7 (c 0.15, CHCl3)Source of chirality: enantiopure reactantAbsolute configuration: (3S)
