Stereospecific route to 5,11-methanomorphanthridine alkaloids via intramolecular 1,3-dipolar cycloaddition of nonstabilized azomethine ylide: formal total synthesis of (+/-)-pancracine.
The core structure of the complex pentacyclic 5,11-methanomorphanthridine alkaloids is constructed stereospecifically in one step employing an intramolecular [3 + 2]-cycloaddition of nonstabilized azomethine ylide as the key step. The strategy is demonstrated by accomplishing the formal total synthesis of (+/-)-pancracine. [reaction: see text]
Pandey
Ganesh
G
Division of Organic Chemistry (Synthesis) and Center for Material Characterization, National Chemical Laboratory, Pune 411008, India. gp.pandey@ncl.res.in
Banerjee
Prabal
P
Kumar
Ravindra
R
Puranik
Vedavati G
VG
D000470:Alkaloids / Q000138:chemical synthesis*; D002384:Catalysis; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
D000470:Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings; C511228:pancracine