Chemoenzymatic Formal Total Synthesis of ent-Codeine and Other Morphinans via Nitrone Cycloadditions and/or Radical Cyclizations. Comparison of Strategies for Control of C-9/C-14 Stereogenic Centers

Formal total syntheses of ent‐codeine and other morphinans were accomplished from 1‐phenyl‐2‐acetoxyethane, which was subjected to enzymatic dihydroxylation by toluene dioxygenase overexpressed in Eschericia coli JM109 (pDTG601A). The resulting cis‐dihydroarenediol was coupled with a phenol derived...

Ausführliche Beschreibung

Bibliographische Detailangaben

Veröffentlicht in:	Advanced synthesis & catalysis 2014-02, Vol.356 (2-3), p.333-339
Hauptverfasser:	Endoma-Arias, Mary Ann A., Hudlicky, Jason Reed, Simionescu, Razvan, Hudlicky, Tomas
Format:	Artikel
Sprache:	eng
Schlagworte:	[3+2] nitrile oxide cycloaddition [3+2] nitrone cycloaddition aldehyde-olefin radical cycloaddition codeine synthesis Cycloaddition enzymatic dihydroxylation Heck reaction Olefins Oxides Radicals Spectra Strategy Synthesis Toluene
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!