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- Title
Synthesis of Enantiomeric Pure E-Nor-15-azayohimbines.
- Authors
Valls, Nativitat; Bonjoch, Josep; Del Alamo, Carlos; Bosch, Joan
- Abstract
A stereodivergent synthesis of enantiomerically pure E-nor-15-azayohimbines via condensation of tryptamine with derivatives of pyroglutamate 4 is reported. When the Pictet- Spengler reaction was induced in refluxing aqueous AcOH a nearly equimolar ratio of lactams 7 and 8 was obtained, whereas under kinetic control (TFA, room temperature) the trans-derivative 8 was the major product. In contrast, cyclization of amido acetal 12 with TsOH gave the cis-derivative 7 as preponderant component.
- Publication
Helvetica Chimica Acta, 1992, Vol 75, Issue 1, p137
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19920750110