Please use this identifier to cite or link to this item:
Title: Structural revision of Stemoburkilline from an E-alkene to a Z-alkene
Authors: Kwankamol Sastraruji
Stephen G. Pyne
Alison T. Ung
Pitchaya Mungkornasawakul
Wilford Lie
Araya Jatisatienr
Keywords: Biochemistry, Genetics and Molecular Biology
Pharmacology, Toxicology and Pharmaceutics
Issue Date: 1-Feb-2009
Abstract: Semisynthesis studies starting from (11Z)-1′,2′- didehydrostemofoline (4) indicated that the known Stemona alkaloid stemoburkilline is the Z-isomer and not the E-isomer as initially reported. The semisynthesis involved conversion of (11Z)-1′,2′- didehydrostemofoline (4) to 11(S),12(S)-dihydrostemofoline (3) followed by a stereoselective base-catalyzed ring-opening reaction to give (Z)-stemoburkilline (8). The same product was obtained using a similar synthetic protocol starting from isostemofoline (6) via a based-catalyzed ring-opening reaction of 11(S),12(R)-dihydrostemofoline (1). A re-examination of the crude root extracts of Stemona burkillii Prain and further NOE studies established stemoburkilline as the Z-isomer (8). © 2009 American Chemical Society and American Society of Pharmacognosy.
ISSN: 01633864
Appears in Collections:CMUL: Journal Articles

Files in This Item:
There are no files associated with this item.

Items in CMUIR are protected by copyright, with all rights reserved, unless otherwise indicated.