Intramolecular 5-endo-trig aminomercuration of beta-hydroxy-gamma-alkenylamines: efficient route to a pyrrolidine ring and its application for the synthesis of (+)-castanospermine and analogues.
The intramolecular aminomercuration reaction of sugar-derived beta-hydroxy-gamma-alkenylamines 8a-c undergoes 5-endo-trig cyclization in high yield. The sugar-substituted pyrrolidines thus obtained were elaborated to the synthesis of polyhydroxylated indolizidine alkaloids, namely, castanospermine 1a, 1-epi-castanospermine 1b, and 8a-epi-castanospermine 1c, having promising glycosidase inhibitory activities.
Karanjule
Narayan S
NS
Department of Chemistry, Garware Research Centre, University of Pune, Pune-411 007, India.
Markad
Shankar D
SD
Shinde
Vaishali S
VS
Dhavale
Dilip D
DD
D000588:Amines / Q000737:chemistry; D003500:Cyclization; D005959:Glucosidases / Q000037:antagonists & inhibitors; D007212:Indolizines / Q000138:chemical synthesis*; D008628:Mercury / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis*; D054836:Indolizidines
D000588:Amines; D005959:Glucosidases; D007212:Indolizines; D008628:Mercury; D011759:Pyrrolidines; C037806:castanospermine; D054836:Indolizidines