| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348768 | Tetrahedron: Asymmetry | 2006 | 5 Pages |
(2S,3S)-(+)-Thiomicamine 3, a commercially available aminodiol, was transformed into (4R,5S)-5-hydroxymethyl-4-(p-methylthiophenyl)-2-oxazolidinone 10, a compound related to cytoxazone-type biologically active natural products. The synthetic strategy of the highly regio- and stereoselective synthesis was based upon the reversal of the position of the hydroxyl and amine functionalities in 3, accomplished via azidolysis of the key intermediate, epoxide 6.
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(1S,2S)-2-Dimethylamino-1-(4-methylthiophenyl)-1,3-propanediolC12H19NO2S[α]D = +35.6 (c 1.0, MeOH)Source of chirality: (+)-thiomicamineAbsolute configuration: (1S,2S)
(1S,2S)-2-Dimethylamino-1-(4-methylthiophenyl)-1,3-propanediol methiodideC13H22NO2SI[α]D = +46.1 (c 0.98, MeOH)Source of chirality: (+)-thiomicamineAbsolute configuration: (1S,2S)
(2R,3S)-2,3-Epoxy-3-(4-methylthiophenyl)-1-propanolC10H12O2S[α]D = +41.6 (c 0.97, MeOH)Source of chirality: (+)-thiomicamineAbsolute configuration: (2R,3S)
(2S,3R)-3-Azido-3-(4-methylthiophenyl)-1,2-propanediolC10H13N3O2S[α]D = −200.2 (c 0.98, MeOH)Source of chirality: (+)-thiomicamineAbsolute configuration: (2S,3R)
(2S,3R)-3-Azido-1,2-diphenyloxycarbonyloxy-3-(4-methylthiophenyl)-propaneC24H21N3O6S[α]D = −44.7 (c 0.86, MeOH)Source of chirality: (+)-thiomicamineAbsolute configuration: (2S,3R)
(4R,5S)-4-(4-Methylthiophenyl)-5-phenyloxycarbonyloxy-2-oxazolidinoneC18H17NO5S[α]D = +72.2 (c 0.64, MeOH)Source of chirality: (+)-thiomicamineAbsolute configuration: (4R,5S)
(4R,5S)-5-Hydroxymethyl-4-(4-methylthiophenyl)-2-oxazolidinoneC11H13NO3S[α]D = +31.9(c 0.9, MeOH)Source of chirality: (+)-thiomicamineAbsolute configuration: (4R,5S)
