DIASTEREOSELECTIVE TOTAL SYNTHESIS OF SIBIRINE VIA FUNCTIONALIZED IMINE PRECURSORS

Authors
KEPPENS M DEKIMPE N
Citation
M. Keppens et N. Dekimpe, DIASTEREOSELECTIVE TOTAL SYNTHESIS OF SIBIRINE VIA FUNCTIONALIZED IMINE PRECURSORS, Synlett, (4), 1994, pp. 285-286
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
4
Year of publication
1994
Pages
285 - 286
Database
ISI
SICI code
0936-5214(1994):4<285:DTSOSV>2.0.ZU;2-W
Abstract
The spirocyclic alkaloid (+/-)-sibirine was prepared in a straightforw ard way from an easily accessible imine precursor. A stabase-mediated alkylation and cyclization process provided an azaspirocyclic intermed iate, which was converted stereoselectively to (+/-)-sibirine via a co nvenient four step sequence including a stereoselective cerium-catalyz ed reduction. The first two steps of this sequence also constitute a f ormal synthesis of (+/-)-nitramine.