Abstract
The semisynthesis of the Stemona alkaloids (3'R)-stemofolenol (1), (3'S)-stemofolenol (2), methylstemofoline (3), and (3'S)-hydroxystemofoline (5) and the unnatural analogues (11E)-methylstemofoline (15) and 3'R-hydroxystemofoline (11) has been achieved starting from (11Z)-1',2'-didehydrostemofoline (4). This synthesis allowed, for the first time, access to diastereomerically enriched samples of 1 and 2 and the assignment of their absolute configurations at C-3'. These compounds were obtained in sufficient quantities to allow for their biological testing. In a quantitative assay as AChE inhibitors, (11Z)-1',2'-didehydrostemofoline (4) and (3'S)-hydroxystemofoline (5) were found to be the most active.
Publication types
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Alkaloids / chemical synthesis*
-
Alkaloids / chemistry
-
Alkaloids / pharmacology
-
Candida albicans / drug effects
-
Cholinesterase Inhibitors / chemical synthesis*
-
Cholinesterase Inhibitors / chemistry
-
Cholinesterase Inhibitors / pharmacology
-
Escherichia coli / drug effects
-
Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
-
Heterocyclic Compounds, 4 or More Rings / chemistry
-
Heterocyclic Compounds, 4 or More Rings / pharmacology
-
Microbial Sensitivity Tests
-
Molecular Structure
-
Nuclear Magnetic Resonance, Biomolecular
-
Pseudomonas aeruginosa / drug effects
-
Staphylococcus aureus / drug effects
-
Stemonaceae / chemistry*
-
Stereoisomerism
Substances
-
(11Z)-1',2'-didehydrostemofoline
-
(3'S)-hydroxystemofoline
-
Alkaloids
-
Cholinesterase Inhibitors
-
Heterocyclic Compounds, 4 or More Rings
-
didehydrostemofoline
-
stemofoline