One-pot synthesis of highly functionalized morphans from C-glycosides.
Highly functionalized morphan derivatives were synthesized from nitroalkene 2'-(oxoalkyl)-C-glycosides by a tandem reaction that created three (two C-N and one C-C) new bonds and four stereogenic centers in a one-pot procedure under very mild conditions without the use of expensive reagents. The transformation was achieved from a beta-elimination/Michael addition cascade, followed by Michael addition of the amine and intramolecular enamination. In the presence of sodium cyanoborohydride the iminium intermediate was reduced in situ to afford the desired morphans.
Zou
Wei
W
Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario, Canada K1A 0R6. wei.zou@nrc-cnrc.gc.ca
Vembaiyan
Kannan
K
Bhasin
Milan
M
Williams
Dean T
DT
D000473:Alkanes / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D000700:Analgesics / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D006027:Glycosides; D009005:Monosaccharides / Q000737:chemistry*; D009020:Morphine / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D013237:Stereoisomerism; D013379:Substrate Specificity
D000473:Alkanes; D000588:Amines; D000700:Analgesics; C438934:C-glycoside; D006027:Glycosides; D009005:Monosaccharides; D009020:Morphine