| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1343732 | Tetrahedron: Asymmetry | 2015 | 6 Pages |
A short and efficient enantioselective synthesis of yashabushidiols A and B and the β-hydroxy-δ-lactone moiety of compactin and mevinolin with high enantiomeric purity (98% ee) is described starting from commercially available materials. The strategy mainly comprises of iodine-induced intramolecular electrophilic addition of a carbonate occurring in a highly diastereoselective fashion and the Co-catalyzed two-stereocentered hydrolytic kinetic resolution of a functionalized epoxide as the chiral inducing step.
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tert-Butyldimethyl(((R)-1-((R)-oxiran-2-yl)-4-phenylbutan-2-yl)oxy)silaneC18H30O2SiEe 98% determined by chiral HPLC[α]D20 = −5.5 (c 1, CHCl3)Source of chirality: two stereocentered hydrolytic kinetic resolutionAbsolute configuration: (R,R)
(2S,4S)-4-((tert-Butyldimethylsilyl)oxy)-6-phenylhexane-1,2-diolC18H32O3SiEe 96% determined by chiral HPLC[α]D20 = +30.7 (c 1, CHCl3)Source of chirality: two stereocentered hydrolytic kinetic resolutionAbsolute configuration: (S,S)
(3S,5R)-3,5-Dihydroxy-7-phenylheptanenitrileC13H17NO2Ee 98% determined by chiral HPLC[α]D20 = −5.1 (c 0.1, CHCl3)Source of chirality: two stereocentered hydrolytic kinetic resolutionAbsolute configuration: (S,R)
(+)-(4R,6R)-4-Hydroxy-6-(2-phenylethyl)-tetrahydro-2H-pyran-2-oneC13H16O3Ee 98% determined by chiral HPLC[α]D20 = +67.5 (c 2, CHCl3)Source of chirality: two stereocentered hydrolytic kinetic resolutionAbsolute configuration: (R,R)
(2S,4S)-4-((tert-Butyldimethylsilyl)oxy)-2-hydroxy-6-phenylhexyl pivalateC23H40O4SiEe 96% determined by chiral HPLC[α]D20 = +6.5 (c 0.8, CHCl3)Source of chirality: hydrolytic kinetic resolutionAbsolute configuration: (S,S)
(2S,4S)-4-((tert-Butyldimethylsilyl)oxy)-2-((methylsulfonyl)oxy)-6-phenylhexyl pivalateC24H42O6SSiEe 96% determined by chiral HPLC[α]D20 = +7.5 (c 1, MeOH)Source of chirality: hydrolytic kinetic resolutionAbsolute configuration: (S,S)
tert-Butyldimethyl(((S)-1-((R)-oxiran-2-yl)-4-phenylbutan-2-yl)oxy)silaneC18H30O2SiEe 96% determined by chiral HPLC[α]D20 = +4.8 (c 1, CHCl3)Source of chirality: hydrolytic kinetic resolutionAbsolute configuration: (S,R)
(3S,5S)-1,7-Diphenylheptane-3,5-diolC19H24O2Ee 96% determined by chiral HPLC[α]D20 = −7.0 (c 1, CHCl3)Source of chirality: hydrolytic kinetic resolutionAbsolute configuration: (S,S)
