DIASTEREOSPECIFIC SYNTHESIS OF SPIRO[4.5]DECAN-2-ONES AS VETIVANE PRECURSOR VIA RHODIUM-CATALYZED CLAISEN REARRANGEMENT HYDROACYLATION/

Authors
SATTELKAU T EILBRACHT P
Citation
T. Sattelkau et P. Eilbracht, DIASTEREOSPECIFIC SYNTHESIS OF SPIRO[4.5]DECAN-2-ONES AS VETIVANE PRECURSOR VIA RHODIUM-CATALYZED CLAISEN REARRANGEMENT HYDROACYLATION/, Tetrahedron letters, 39(14), 1998, pp. 1905-1908
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
14
Year of publication
1998
Pages
1905 - 1908
Database
ISI
SICI code
0040-4039(1998)39:14<1905:DSOSAV>2.0.ZU;2-J
Abstract
The one-pot combination of Claisen rearrangement of allyl vinyl ethers followed by an intramolecular hydroacylation catalysed by RhCl(cod)(d ppe) is used as a key step in the synthesis of methyl-1,4-dioxa-dispir o[4.2.4.2]tetradecan-10-one (12). The diastereospecific outcome of the reaction is discussed. This product is a potential precursor in the s ynthesis of solavetivone. (C) 1998 Elsevier Science Ltd. All rights re served.