ol7b01934_si_001.pdf (1.63 MB)
Concurrent Hydrogenation of Three Functional Groups Enables Synthesis of C3′-Homologated Nucleoside Amino Acids
journal contribution
posted on 2017-07-21, 20:31 authored by Venubabu Kotikam, Eriks RoznersInternucleoside amide
linkages are excellent mimics of phosphodiesters
in RNA and may be used to optimize the properties of short interfering
RNAs. Herein we report a remarkably straightforward, efficient and
step economic synthesis of C3′-homologated uridine and adenosine
amino acids starting from nucleosides in six steps (31% overall yield)
and eight steps (16% overall yield), respectively. The key enabling
step is a one-pot multifunctional group transformation including a
stereoselective hydrogenation, termed “Global Hydrogenation”.