Phytochemical studies on Stemona burkillii prain: two new dihydrostemofoline alkaloids.
نویسندگان
چکیده
Two new dihydrostemofoline alkaloids, 11(S),12(R)-dihydrostemofoline (3) and stemoburkilline (4), along with stemofoline (1) and 2'-hydroxystemofoline (2) have been isolated from a root extract of Stemona burkillii Prain. The structure and relative configuration of 3 have been determined via spectroscopic data and from comparison with synthetic 11(S),12(S)-dihydrostemofoline (5). The configuration of the exo-cyclic alkene group in 4 is tentively assigned as E on the basis of mechanistic considerations.
منابع مشابه
Structural revision of stemoburkilline from an E-alkene to a Z-alkene.
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)-stemoburkil...
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عنوان ژورنال:
- Journal of natural products
دوره 67 10 شماره
صفحات -
تاریخ انتشار 2004