Syntheses of new spirocarbocyclic nucleoside analogs using iminonitroso Diels-Alder reactions.
N-Cbz- and Boc-protected spirocyclic dienes were prepared by dialkylation of cyclopentadiene. These dienes coupled efficiently in a series of iminonitroso Diels-Alder reactions to produce a series of new spirocyclic adducts. Hydrogenolysis of these adducts afforded new spirocycles that contain multiple handles for further functionalization. Furthermore, stereocontrolled dihydroxylation and reductive cleavage of the spirocyclic adducts generated versatile scaffolds for the syntheses and derivatization of novel spirocyclic carbocyclic nucleoside analogs.
Lin
Weimin
W
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA.
Gupta
Anuradha
A
Kim
Kyung Hee
KH
Mendel
David
D
Miller
Marvin J
MJ
D006865:Hydrogenation; D007097:Imines / Q000737:chemistry*; D009603:Nitroso Compounds / Q000737:chemistry*; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000737:chemistry*
D007097:Imines; D009603:Nitroso Compounds; D009705:Nucleosides; D013141:Spiro Compounds