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A new synthetic access to bicyclic polyhydroxylated alkaloid analogues from pyranosides.
- Source :
-
Organic & biomolecular chemistry [Org Biomol Chem] 2010 Jun 07; Vol. 8 (11), pp. 2639-49. Date of Electronic Publication: 2010 Apr 07. - Publication Year :
- 2010
-
Abstract
- A facile, versatile and stereoselective synthesis of bicyclic polyhydroxylated alkaloids as castanospermine analogues is described. The synthetic route started from methyl pyranosides. The key steps involved a high-yielding expeditious one-pot tandem reaction from alkenes to N-substituted delta-lactams. The delta-lactams were stereoselectively vinylated to give the dienes, which were followed by the ring-closing metathesis to produce the cyclized products. The functional group transformations of the resulting bicyclic compounds furnished diverse polyhydroxylated alkaloids in good yields.
Details
- Language :
- English
- ISSN :
- 1477-0539
- Volume :
- 8
- Issue :
- 11
- Database :
- MEDLINE
- Journal :
- Organic & biomolecular chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 20376396
- Full Text :
- https://doi.org/10.1039/b923180c