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Synthesis of Enantiomeric Pure E-Nor-15-azayohimbines (1992)

Valls, Nativitat ; Bonjoch, Josep ; Del Alamo, Carlos ; [et al.]

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 75 (1992), S. 137-144

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: 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.

Additional Material: 2 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19920750110

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