Synthesis mediated by ring-closing metathesis - Applications in the synthesis of azasugars and alkaloids

Authors
Pandit, UK Overkleeft, HS Borer, BC Bieraugel, H
Citation
Uk. Pandit et al., Synthesis mediated by ring-closing metathesis - Applications in the synthesis of azasugars and alkaloids, EUR J ORG C, (5), 1999, pp. 959-968
Citations number
71
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
5
Year of publication
1999
Pages
959 - 968
Database
ISI
SICI code
1434-193X(199905):5<959:SMBRM->2.0.ZU;2-V
Abstract
The application of the ring-closing metathesis (RCM) reaction to the constr uction of a wide variety of nitrogen-containing ring systems is described. The examples include pyrrolizidine, indolizidine, and quinolizidine derivat ives related to azasugars. A formal total synthesis of castanospermine (5) is presented. The utilisation of two RCM steps in the synthetic sequence le ading to the multicyclic ABCDE nucleus 7 of the complex alkaloid manzamine A (6) is discussed.