Synthesis of tetrahydro-β-carbolines via radical cyclization of 2-alkenylthioanilides

Heterocycles

Volumn 66, Issue 1, 2005, Pages 241-249

  Iwadate, Manami ^a   Yamashita, Tohru ^a   Tokuyama, Hidetoshi ^a   Fukuyama, Tohru ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33646896738     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-05-S(K)11     Document Type: Article

References (27)

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19. For a total synthesis of (±)-catharanthine based on the similar strategy, see ref. 6.
20. The enantiomeric excess was determined by chiral HPLC column (DAICEL CHIRALCEL OD 4.6 I.D. × 250 mm, n-hexane/i-PrOH, 95/5, flow rate 0.5 mL/min) using the racemic compounds as reference (ee of 9a, 9b, 9c, 9d, and 9e were >99%, >99%, 97%, 96%, and >99%, respectively).
21. The enantiomeric excess was determined by chiral HPLC column (DAICEL CHIRALCEL OD 4.6 I.D. × 250 mm, n-hexane/i-PrOH 90/10-95/5, flow rate 1.0 mL/min) using the racemic compounds as a reference.
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27. 1H NMR spectral analysis of these (+)-MTPA amides using the corresponding (+)-MTPA amides derived from racemic compounds proved that there was no loss of optical purity during the indole formation reaction.