Explorations of stemona alkaloid-inspired analogues: skeletal modification and functional group diversification.
A tandem Diels-Alder/Schmidt reaction provided an efficient route for the exploration of unnatural Stemona alkaloid analogues. Thus, a series of tricyclic scaffolds were efficiently prepared and then elaborated into seven sets of functionalized analogues. These derivatives incorporated appended heterocycles, such as indoles and quinolines, or other diversity-incorporating moieties such as carbamates and amines. Both the scaffold-generation sequence and the diversification steps could be manipulated to provide regio- and diastereochemically pure products.
Frankowski
Kevin J
KJ
Department of Medicinal Chemistry and Center for Chemical Methodologies and Library Development, University of Kansas, Malott Hall, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, USA.
Neuenswander
Benjamin
B
Aubé
Jeffrey
J
D000470:Alkaloids / Q000138:chemical synthesis*; D000588:Amines / Q000737:chemistry; D002219:Carbamates / Q000737:chemistry; D018360:Crystallography, X-Ray; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry; D008956:Models, Chemical; D011804:Quinolines / Q000737:chemistry; D041901:Stemonaceae / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D000588:Amines; D002219:Carbamates; D006571:Heterocyclic Compounds; D007211:Indoles; D011804:Quinolines