Diastereoselective synthesis of a spironoraristeromycin using an acylnitroso Diels-Alder reaction.
The tert-butyl N-hydroxycarbamate-derived nitroso reagent 1 reacted with N-Cbz-protected spirocyclic diene 2 to provide spirocycloadduct 3. Here we describe the efficient conversion of 3 into the novel carbocyclic nucleoside spironoraristeromycin 4.
Lin
Weimin
W
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA.
Virga
Kristopher G
KG
Kim
Kyung-Hee
KH
Zajicek
Jaroslav
J
Mendel
David
D
Miller
Marvin J
MJ
D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D009603:Nitroso Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D009603:Nitroso Compounds; C076829:5'-noraristeromycin; D000241:Adenosine