RIS ID
30831
Abstract
Semisynthesis studies starting from (11Z)-I',2'-didehydrostemofoline 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 to II(S), 12(S)-dihydrostemofoline followed by a stereoselective base-catalyzed ring-opening reaction to give (Z)-stemoburkilline. The same product was obtained using a similar synthetic protocol stariing from isostemofoline via a based-catalyzed ring-opening reaction of II (S), 12(R)-dihydrostemofoline. A re-examination of the crude root extracts of Stemona burkillii Prain and further NOE studies established stemoburkilline as the Z-isomer.
Grant Number
ARC/DP0879491
Additional Grant Number
Included in
Life Sciences Commons, Physical Sciences and Mathematics Commons, Social and Behavioral Sciences Commons
Publication Details
Sastraruji, K., Pyne, S. G., Ung, A. T., Mungkornasawakul, P., Lie, W. & Jatisatienr, A. (2009). Structural revision of stemoburkilline from an E-alkene to a Z-alkene. Journal of Natural Products, 72 (2), 316-318.