| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1346001 | Tetrahedron: Asymmetry | 2012 | 6 Pages |
The stereoselective total synthesis of decarestrictine O, a polyketide natural product is described. The synthesis involves MacMillan α-hydroxylation, C1-Wittig olefination, hydrolytic kinetic resolution and ring closing metathesis (RCM) as key steps. Improved efficiency was achieved by using the DIBAL mediated reductive transformation of trans-dimethyl l-tartrate acetonide into ε-hydroxy α,β-unsaturated ester in a single step.
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(E)-Ethyl 3-((4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylateC11H18O5[α]D25=-6.3 (c 0.5, CHCl3)Source of chirality: Dimethyl l-tartrateAbsolute configuration: (4S,5S)
Ethyl 3-((4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)propanoateC11H20O5[α]D25=+20.3 (c 1.26, CHCl3)Source of chirality: Dimethyl l-tartrateAbsolute configuration: (4S,5S)
Ethyl-3-((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)propanoateC12H20O4[α]D25=+18.7 (c 0.8, CHCl3)Source of chirality: Dimethyl l-tartrate and stereoselective synthesisAbsolute configuration: (4S,5S)
3-((4S,5S)-2,2-Dimethyl-5-vinyl-1,3-dioxolan-4-yl)propan-1-olC10H18O3[α]D25=-16.2 (c 0.4, CHCl3)Source of chirality: Dimethyl l-tartrate and stereoselective synthesisAbsolute configuration: (4S,5S)
(S)-3-((4S,5S)-2,2-Dimethyl-5-vinyl-1,3-dioxan-4-yl) propane-1,2-diolC10H18O4[α]D25=-2.5 (c 0.2, CHCl3)Source of chirality: stereoselective synthesisAbsolute configuration: (3S,4S,5S)
(S)-3-(4S,5S)-2,2-Dimethyl-5-vinyl-1,3-dioxolan-4-yl)-2-hydroxypropyl4-methyl benzenesulfonateC17H24O6S[α]D25=-65.3 (c 0.4, CHCl3)Source of chirality: stereoselective synthesisAbsolute configuration: (3S,4S,5S)
(R)-1-((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)propan-2-olC10H18O3[α]D25=-12.25 (c 0.4, CHCl3)Source of chirality: stereoselective synthesisAbsolute configuration: (2R,4S,5S)
(S)-2-(2-(Benzyloxy)ethyl)oxiraneC11H14O2[α]D25=+19.2 (c 0.7, CHCl3)Source of chirality: Stereoselective synthesisAbsolute configuration: (2S)
(S)-5-(Benzyloxy)pent-1-en-3-olC12H16O2[α]D25=-2.1 (c 0.6, CHCl3)Source of chirality: stereoselective synthesisAbsolute configuration: (3S)
(S)-(5-(Benzyloxy)pent-1-en-3-yloxy)(tert-butyl)dimethylsilaneC18H30O2Si[α]D25=+6.4 (c 0.4, CHCl3)Source of chirality: stereoselective synthesisAbsolute configuration: (3S)
(S)-3-(tert-Butyldimethylsilyloxy)pent-4-en-1-olC11H24O2Si[α]D25=+4.7 (c 0.6, CHCl3)Source of chirality: stereoselective synthesisAbsolute configuration: (3S)
(S)-((R)-1-((4S,5S)-2,2-Dimethyl-5-vinyl-1,3-dioxolan-4-yl)propan-2-yl) 3-(tertbutyldimethylsilyloxy)pent-4-enoateC21H38O5Si[α]D25=-5.25 (c 0.4, CHCl3)Source of chirality: stereoselective synthesisAbsolute configuration: (2R,4S,5S,31S)
(3S,5R,9S,11S,E)-9-(tert-Butyl dimethyl silyloxy)-2,2,5-trimethyl-4,5,8,9-tetrahydro-3-(1,3)dioxolo(4,5)oxecin-7-oneC19H34O5Si[α]D25=-8.1 (c 0.4, CHCl3)Source of chirality: stereoselective synthesisAbsolute configuration: (3S,5R,9S,11S)
(4S,7S,8S,10R,E)-4,7,8-Trihydroxy-10-methyl-3,4,7,8,9,10-hexahydro-2H-oxecin-2-oneC10H16O5[α]D25=-21.8 (c 0.2, CHCl3)Source of chirality: stereoselective synthesisAbsolute configuration: (4S,7S,8S,10R)
