A modified Sandmeyer methodology and the synthesis of (±)-convolutamydine A

Tetrahedron Letters

Volumn 38, Issue 9, 1997, Pages 1501-1504

  Garden, Simon J ^a   Torres, José C ^a   Ferreira, Alexandre A ^a   Silva, Rosangela B ^a   Pinto, Angelo C ^a  

^a FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CONVOLUTAMYDINE A; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION TIME; STEREOISOMERISM;

EID: 0031550864     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00140-8     Document Type: Article

References (21)

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9. 2O, 10g NaOH, 100°C) over a period of 15 minutes. Digestion was continued for a further 2.5 hours (110°C). The catalyst was filtered by suction, washed with water (80 ml in small portions) then ethanol (40 ml) and transfered as an ethanolic suspension to the hydrogenation bottle. At no time was the catalyst allowed to become dry.
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15. 8d
16. 10. At the same time, however, it is necessary that the ethanol be allowed to evaporate from the reaction mixture in order that the isonitrosoacetanilide may precipitate. A procedure has been developed where the ethanol is not allowed to evaporate from the reaction mixture (by use of a condensor) until TLC indicates that isonitrosoacetanilide formation is complete, the reaction temperature is maintained at 80°C through all processes.
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18. 12. In a model study of the reaction of isatin with acetone, at fixed concentration, using varying quantities of S(-)-proline, no asymmetric induction was observed in the final product as determined by measurement of optical rotation at various concentrations after isolation of the product.
19. 3: C, 36.40; H, 2.50; N, 3.86; Found: C, 36.27; H, 2.43; N, 3.96.
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21. 79BrN].