| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1345896 | Tetrahedron: Asymmetry | 2013 | 7 Pages |
A divergent and scalable asymmetric synthesis of the dopamine D1 agonists, A-86929, and dihydrexidine with high diastereo- and enantioselectivity was accomplished from Weinreb amide 8 derived from inexpensive and easily available l-serine. The synthesis of A-86929 involves only one chromatographic purification.
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(R)-tert-Butyl 4-(3,4-dimethoxyphenethyl)-2,2-dimethyloxazolidine-3-carboxylateC20H31NO5Ee >98%[α]D25=-37.7 (c 0.51, CHCl3)Source of chirality: l-serineAbsolute configuration: (R)
(R)-tert-Butyl (4-(3,4-dimethoxyphenyl)-1-hydroxybutan-2-yl)carbamateC17H27NO5Ee >98%[α]D25=+9.3 (c 0.77, CHCl3)Source of chirality: l-serineAbsolute configuration: (R)
(R)-2-((tert-Butoxycarbonyl)amino)-4-(3,4-dimethoxyphenyl)butanoic acidC17H25NO6Ee >98%[α]D25=+4.1 (c 0.51, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
(R)-tert-Butyl (4-(3,4-dimethoxyphenyl)-1-(methoxy(methyl)amino)-1-oxobutan-2-yl)carbamateC19H30N2O6Ee >98%[α]D25=+11 (c 0.51, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
(R)-tert-Butyl (4-(3,4-dimethoxyphenyl)-1-oxo-1-(5-propylthiophen-3-yl)butan-2-yl)carbamate 15C24H33NO5SEe >98%[α]D25=-28.5 (c 0.39, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
(5aR,11bS)-9,10-Dimethoxy-2-propyl-4,5,5a,6,7,11b-hexahydrobenzo[f]thieno[2,3-c]quinoline hydrochlorideC20H26ClNO2SDr >99:1Ee >99%[α]D25=-243.3 (c 0.55, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (5aR,11bS)
(5aR,11bS)-2-Propyl-4,5,5a,6,7,11b-hexahydrobenzo[f]thieno[2,3-c]quinoline-9,10-diol hydrobromideC18H22BrNO2SEe >99%[α]D25=-176.2 (c 1.0, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (5aR,11bS)
(R)-tert-Butyl (4-(3,4-dimethoxyphenyl)-1-oxo-1-phenylbutan-2-yl)carbamateC23H29NO5Ee >98%[α]D25=-24.7 (c 2.95, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
N-((1R,2R)-6,7-Dimethoxy-1-phenyl-1,2,3,4-tetrahydronaphthalen-2-yl)-4-nitrobenzenesulfonamideC24H24N2O6SEe >99%[α]D25=-64.4 (c 0.96, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (1R,2R)
