| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1347467 | Tetrahedron: Asymmetry | 2009 | 7 Pages |
The first synthesis of (+)-myxothiazol A 1 was achieved based on a modified Julia olefination between (3,5R)-dimethoxy-(4R)-methyl-6-oxo-(2E)-hexenamide 3, corresponding to the left side of the final molecule, and 4-(2″-benzothiazolyl)sulfonylmethyl-2′-[(1′″R),6′″-dimethylhepta-(2′″E),(4′″E)-dienyl]-2,4′-bithiazole 6, corresponding to the right side. The synthesis of (+)-myxothiazol Z 2 was also achieved based on modified Julia olefination between (3,5R)-dimethoxy-(4R)-methyl-6-oxo-(2E)-hexenoate 4, corresponding to left side of the final molecule, and (S)-sulfone 6.
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n-Butyl 2-hydroxy-3-methyl-5-trimethylsilyl-4-pentynoateC13H24O3SiEe = >99%[α]D24=-7.6 (c 1.09, CHCl3)Source of chirality: lipaseAbsolute configuration: (2R,3S)
n-Butyl 3-methyl-2-methoxy-5-trimethylsilyl-4-pentynoateC14H26O3SiEe = >99%[α]D24=+0.8 (c 1.54, CHCl3)Source of chirality: lipaseAbsolute configuration: (2R,3S)
3-Methyl-2-methoxy-5-trimethylsilyl-4-pentyn-1-olC7H12O2Ee = >99%[α]D27=-27.6 (c 1.05, CHCl3)Source of chirality: lipaseAbsolute configuration: (2R,3S)
tert-Butyldimethylsiloxy-3-methyl-2-methoxy-4-pentynC13H26O2SiEe = >99%[α]D25=-4.7 (c 1.06, CHCl3)Source of chirality: lipaseAbsolute configuration: (2R,3S)
Methyl 6-tert-butyldimethylsiloxy-4-methyl-5-methoxy-2-hexynoateC15H28O4SiEe = >99%[α]D24=-15.1 (c 0.86, CHCl3)Source of chirality: lipaseAbsolute configuration: (4S,5R)
Methyl 6-tert-butyldimethylsiloxy-3,5-dimethoxy-4-methyl-2(Z)-hexenoateC16H32O5SiEe = >99%[α]D24=-15.6 (c 0.96, CHCl3)Source of chirality: lipaseAbsolute configuration: (4R,5R)
Methyl 6-tert-butyldimethylsiloxy-3,5-dimethoxy-4-methyl-2(E)-hexenamideC15H31NO4SiEe = >99%[α]D27=+35.7 (c 0.84, CHCl3)Source of chirality: lipaseAbsolute configuration: (4R,5R)
Methyl 3,5-dimethoxy-4-methyl-6-oxo-(2E)-hexenoateC10H16O5Ee = >99%[α]D23=+104.7 (c 0.55, CHCl3)Source of chirality: lipaseAbsolute configuration: (4R,5R)
4-Ethoxycarbonyl-2′-(1-benzothiazolylsulfanyl-methylethyl)-2,4′-bithiazoleC19H17N3O2S4Ee = >99%[α]D26=-92.9 (c 1.48, CHCl3)Source of chirality: lipaseAbsolute configuration: (S)
4-Benzothiazolylsulfanylmethyl-2′-(1-benzo-thiazolylsulfonylmethylethyl)-2,4′-bithiazoleC24H18N4O2S6Ee = >99%[α]D26=-74.4 (c 0.77, CHCl3)Source of chirality: lipaseAbsolute configuration: (S)
4-(2″-Benzothiazolyl)sulfanylmethyl-2′-[1″′,6″′-dimethylhepta-(2″′E),(4″′E)-dienyl]-2,4′-bithiazoleC23H23N3SEe = >99%[α]D27=+7.8 (c 0.525, CHCl3)Source of chirality: lipaseAbsolute configuration: (S)
Myxothiazol AC25H33N3O3S2Ee = >99%[α]D26=+33.5 (c 0.70, MeOH)Source of chirality: lipaseAbsolute configuration: (4R,5S,1S)
Myxothiazol ZC26H34N2O4S2Ee = >99%[α]D27=+85.7 (c 1.66, MeOH)Source of chirality: lipaseAbsolute configuration: (4R,5S,1S)
