Scaffold diversity through intramolecular cascade reactions of solid-supported cyclic N-acyliminium intermediates
Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
The solid-phase synthesis of pharmacologically interesting heterocycles is presented. The formation of a series of (5,5)-, (5,6)-, (6,5)-, and (6,6)-fused bicyclic ring systems was systematically studied by implementation of a common strategy involving N-acyliminium intermediates. These are highly reactive and transformed further in intramolecular cascade reactions with strong as well as weak C, N, S, and 0-nucleophiles. The methodology was successfully applied to the conversion of peptidomimetics into constrained small molecule core structures, such as the hexahydropyrrolo[2,1-b][1,3]oxazines, generally with full control of diastereoselectivity (>20:1) and in purities above 90%.
Originalsprog | Engelsk |
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Tidsskrift | Journal of Combinatorial Chemistry |
Vol/bind | 9 |
Udgave nummer | 6 |
Sider (fra-til) | 1060-1072 |
Antal sider | 13 |
ISSN | 1520-4766 |
DOI | |
Status | Udgivet - nov. 2007 |
Eksternt udgivet | Ja |
ID: 321882391