Scaffold diversity through intramolecular cascade reactions of solid-supported cyclic N-acyliminium intermediates
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Scaffold diversity through intramolecular cascade reactions of solid-supported cyclic N-acyliminium intermediates. / Le Quement, Sebastian T.; Nielsen, Thomas E.; Meldal, Morten.
I: Journal of Combinatorial Chemistry, Bind 9, Nr. 6, 11.2007, s. 1060-1072.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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TY - JOUR
T1 - Scaffold diversity through intramolecular cascade reactions of solid-supported cyclic N-acyliminium intermediates
AU - Le Quement, Sebastian T.
AU - Nielsen, Thomas E.
AU - Meldal, Morten
PY - 2007/11
Y1 - 2007/11
N2 - 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%.
AB - 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%.
UR - http://www.scopus.com/inward/record.url?scp=36749090670&partnerID=8YFLogxK
U2 - 10.1021/cc700097k
DO - 10.1021/cc700097k
M3 - Journal article
C2 - 17994787
AN - SCOPUS:36749090670
VL - 9
SP - 1060
EP - 1072
JO - ACS Combinatorial Science
JF - ACS Combinatorial Science
SN - 2156-8952
IS - 6
ER -
ID: 321882391