Total synthesis of (-)-halosaline by a ruthenium-catalyzed ring rearrangement

Authors
Stragies, R Blechert, S
Citation
R. Stragies et S. Blechert, Total synthesis of (-)-halosaline by a ruthenium-catalyzed ring rearrangement, TETRAHEDRON, 55(27), 1999, pp. 8179-8188
Citations number
26
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
27
Year of publication
1999
Pages
8179 - 8188
Database
ISI
SICI code
0040-4020(19990702)55:27<8179:TSO(BA>2.0.ZU;2-A
Abstract
The stereoselective synthesis of substituted piperidines by a ruthenium-cat alyzed ring rearrangement of cyclopentene derivatives is demonstrated. The influence of different substituents and the effect of ethylene on the metat hesis reaction is described. The ring rearrangement can be combined with a molybdenum-catalyzed cross metathesis reaction using allyltrimethyl silane as coupling partner. The first total synthesis of (-)-halosaline was accomp lished via domino metathesis reaction utilizing Grubbs' ruthenium catalyst, (C) 1999 Elsevier Science Ltd. All rights reserved.