| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1346308 | Tetrahedron: Asymmetry | 2011 | 8 Pages |
A scalable asymmetric synthesis of trans-2-amino-6,7-dimethoxy-1-phenyltetralin 2 and its N-nosyl derivative 12 have been achieved from Garner aldehyde derived from easily available d-serine using a stereoselective PhMgBr addition, Wittig reaction and TFA-mediated Friedel–Crafts cyclization as the key steps. The synthesis of dihydrexidine is accomplished from the N-nosyl-2-amino-1-phenyltetralin 12.
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(R)-4-{(R)-Hydroxyphenylmethyl}-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl esterC17H25NO4Ee = 97.8%[α]D25=-19.0 (c 1.0, CHCl3)Source of chirality: d-serineAbsolute configuration: (R,R)
(R)-4-[(R)-(tert-Butyldimethylsilanyloxy)phenylmethyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl esterC23H39NO4SiEe = 93.8%[α]D25=+62.2 (c 1.01, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,R)
[(1R,2R)-2-(tert-Butyldimethylsilanyloxy)-1-hydroxymethyl-2-phenylethyl]-carbamic acid tert-butyl esterC20H35NO4SiEe = 93.7%[α]D25=-31.3 (c 1.0,CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (1R,2R)
[(R)-1-[(R)-(tert-Butyldimethylsilanyloxy)-phenylmethyl]-3-(3,4-dimethoxyphenyl)-propyl]-carbamic acid tert-butyl esterC29H45NO5SiEe = 96.4%[α]D25=-5.7 (c 0.85, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,R)
[(R)-3-(3,4-Dimethoxyphenyl)-1-(R)-hydroxyphenylmethyl)-propyl]-carbamic acid tert-butyl esterC23H31NO5Ee = 92.6%[α]D25=-5.5 (c 1.04, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R,R)
(1S,2R)-N-(6,7-Dimethoxy-1-phenyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-4-nitro-benzenesulfonamideC24H24N2O6SEe = 98.4%[α]D25=-64.2 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (1S,2R)
(1S,2R)-N-(6,7-Dimethoxy-1-phenyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-N-methoxymethyl-4-nitro-benzenesulfonamideC26H28N2O7SEe = 99.7%[α]D25=-52.2 (c 0.99, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (1S,2R)
(6aR,12bS)-10,11-Dimethoxy-6-(4-nitrobenzenesulfonyl)-5,6,6a,7,8,12b-hexahydrobenzo[a]phenanthridineC25H24N2O6SEe >99%[α]D25=+38.8 (c 0.37, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (6aR,12bS)
(6aR,12bS)-10,11-Dimethoxy-5,6,6a,7,8,12b-hexahydrobenzo[a]phenanthridineC19H22ClNO2Ee >99%[α]D25=+110.0 (c 0.15, EtOH)Source of chirality: asymmetric synthesisAbsolute configuration: (6aR,12bS)
(6aR,12bS)-10,11-Dihydroxy-5,6,6a,7,8,12b-hexahydrobenzo[a]phenanthridine hydrobromideC17H18BrNO2Ee >99%[α]D25=+59 (c 0.21, EtOH)Source of chirality: asymmetric synthesisAbsolute configuration: (6aR,12bS)
(6aR,12bS)-10,11-Dihydroxy-5,6,6a,7,8,12b-hexahydrobenzo[a]phenanthridine hydrochlorideC17H18ClNO2Ee >99.9%[α]D26=+85 (c 0.25, EtOH)Source of chirality: asymmetric synthesisAbsolute configuration: (6aR,12bS)
