Synthesis of 15-azayohimban, a new heterocyclic ring system
1991; Elsevier BV; Volume: 47; Issue: 6 Linguagem: Inglês
10.1016/s0040-4020(01)80944-3
ISSN1464-5416
AutoresNativitat Vails, Vı́ctor Segarra, Maillo Luisa C, Joan Bosch,
Tópico(s)Advanced Synthetic Organic Chemistry
ResumoTwo synthetic routes to the 15-azayohimban ring system have been studied. The first one, based on a Pictet-Spengler condensation between tryptamine and piperidine acetal 4, gave very low yields of pentacycles 2a. The second, more efficient route involves as the crucial step a cyclization of a N-acyliminium cation generated from imide 11. The different course of the Pictet-Spengler reaction from amino acetals 4 and 8, as compared with amido acetal 7, is discussed.
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