Titelaufnahme

Titel
Biocatalytic Organic Synthesis of Optically Pure (S)-Scoulerine and Berbine and Benzylisoquinoline Alkaloids
VerfasserSchrittwieser, Joerg H. ; Resch, Verena ; Wallner, Silvia ; Lienhart, Wolf-Dieter ; Sattler, Johann H. ; Resch, Jasmin ; Macheroux, Peter ; Kroutil, Wolfgang In der Gemeinsamen Normdatei der DNB nachschlagen
Erschienen in
Journal of Organic Chemistry, Washington, DC [u.a.], 2011, Jg. 76, H. 16, S. 6703-6714
ErschienenAmerican Chemical Society
SpracheEnglisch
DokumenttypAufsatz in einer Zeitschrift
ISSNAC00062144
URNurn:nbn:at:at-ubg:3-97 Persistent Identifier (URN)
DOIdoi:10.1021/jo201056f 
Zugriffsbeschränkung
 Das Werk ist frei verfügbar
Dateien
Biocatalytic Organic Synthesis of Optically Pure (S)-Scoulerine and Berbine and Benzylisoquinoline Alkaloids [1.26 mb]
Links
Nachweis
Klassifikation
Zusammenfassung (Englisch)

A chemoenzymatic approach for the asymmetric total synthesis of the title compounds is described that employs an enantioselective oxidative CC bond formation catalyzed by berberine bridge enzyme (BBE) in the asymmetric key step. This unique reaction yielded enantiomerically pure (R)-benzylisoquinoline derivatives and (S)-berbines such as the natural product (S)-scoulerine, a sedative and muscle relaxing agent. The racemic substrates rac-1 required for the biotransformation were prepared in 48 linear steps using either a BischlerNapieralski cyclization or a C1C alkylation approach. The chemoenzymatic synthesis was applied to the preparation of fourteen enantiomerically pure alkaloids, including the natural products (S)-scoulerine and (R)-reticuline, and gave overall yields of up to 20% over 59 linear steps.

Notiz