A chiral hexahydroindolizine as key intermediate in the synthesis of tri- and tetrahydroxyindolizidines

Authors
Lennartz, M Steckhan, E
Citation
M. Lennartz et E. Steckhan, A chiral hexahydroindolizine as key intermediate in the synthesis of tri- and tetrahydroxyindolizidines, TETRAHEDRON, 57(4), 2001, pp. 675-680
Citations number
10
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
4
Year of publication
2001
Pages
675 - 680
Database
ISI
SICI code
0040-4020(20010121)57:4<675:ACHAKI>2.0.ZU;2-R
Abstract
The highly stereoselective functionalization of hexahydro-3-oxo-indolizine 6 has been examined. The bishydroxylated product can be transformed success fully into the trihydroxyindolizidine 11 in 57% overall yield. in addition, a simple elimination process to give the a,P-unsaturated lactam 13 and a s econd highly stereoselective bishydroxylation can be used to synthesise the tetrahydroxyindolizidine 19 in 30% overall yield. (C) 2001 Published by El sevier Science Ltd.