Creation of quaternary stereocentres: synthesis of new polyhydroxylated indolizidines

Creation of quaternary stereocentres: synthesis of new polyhydroxylated indolizidines

(6R,7S,8aR)- and (6S,7R,8aR)-8a-tert-butyldimethylsilyloxymethyl-6,7-dihydroxy-indolizidin-3-ones 14 and 15 were synthesized from bicyclic silyloxypyrrole 2 by the selective formation of a quaternary stereogenic centre and a ring-closing metathesis as the main steps. They were converted into new pol...

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Veröffentlicht in:Tetrahedron: asymmetry 2006-01, Vol.17 (1), p.53-60
Hauptverfasser: Langlois, Nicole, Le Nguyen, Bao Khanh, Retailleau, Pascal, Tarnus, Céline, Salomon, Emmanuel
Format: Artikel
Sprache:eng
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Chemical Sciences
Organic chemistry
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Zusammenfassung:(6R,7S,8aR)- and (6S,7R,8aR)-8a-tert-butyldimethylsilyloxymethyl-6,7-dihydroxy-indolizidin-3-ones 14 and 15 were synthesized from bicyclic silyloxypyrrole 2 by the selective formation of a quaternary stereogenic centre and a ring-closing metathesis as the main steps. They were converted into new polyhydroxyindolizidines 20 and 21 with high diastereoselectivity.
ISSN:0957-4166
1362-511X
0957-4166
DOI:10.1016/j.tetasy.2005.11.017