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OgCii THF* H CHaOGC 7 N pyridine P^"^^"' k^N^si^N DMF* H TsO- 49 k A H^ ^ M^o" kJsAl^'' NC- 50 Scheme (12). Lounasmaa et al synthesis of deethylebumamonine (3). After the correct stereochemistry at C-12b had been obtained, the methyl ester group was reduced with lithium aluminium hydride to yield alcohol 48. Tosylation of the alcohol and subsequent replacement of the tosylate with cyanide resulted in nitrile 50. Finally, acid treatment of 50 resulted in the target compound, deethylebumamonine (3).
They demonstrated that, under acidic conditions, the pure enantiomers racemized with relative ease, and suggested that the racemization resembled epimerization of reserpine (1) and 1,3-disubstituted tetrahydrop-carbolines. Therefore, the mechanism responsible for the racemization would be one of those mentioned above. CH3O CH30 H CH3 39 u 40 NH -> H CH3 NH CH3O H CH3 41 Fig. (10). (+)-Tetrahydroharmine (39), (-)-tetrahydroharmine (40), and (-)-tetrahydroroeharmine (41). Cook and co-workers suggested that partial racemization had occurred in the acid/base mediated isolation of (-)-tetrahydroroeharmine (41), Fig.
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