SYNTHESIS OF CASUARINES [PENTAHYDROXYLATED PYRROLIZIDINES] BY SODIUM-HYDROGEN TELLURIDE-INDUCED CYCLIZATIONS OF AZIDODIMESYLATES

Authors
BELL AA PICKERING L WATSON AA NASH RJ PAN YT ELBEIN AD FLEET GWJ
Citation
Aa. Bell et al., SYNTHESIS OF CASUARINES [PENTAHYDROXYLATED PYRROLIZIDINES] BY SODIUM-HYDROGEN TELLURIDE-INDUCED CYCLIZATIONS OF AZIDODIMESYLATES, Tetrahedron letters, 38(33), 1997, pp. 5869-5872
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
33
Year of publication
1997
Pages
5869 - 5872
Database
ISI
SICI code
0040-4039(1997)38:33<5869:SOC[PB>2.0.ZU;2-I
Abstract
The key step in the synthesis of four diastereomers of casuarine from eight carbon sugar lactones is the efficient reduction of open chain a zidodimesylates by sodium hydrogen telluride [Suzuki-Takaoka reduction ] to allow the formation of the pyrrolizidine nucleus by bicyclisation . This is the first report of the synthesis of such highly oxygenated pyrrolizidines. (C) 1997 Elsevier Science Ltd.