Transition-metal-controlled synthesis of (.+-.)-aristeromycin and (.+-.)-2',3'-diepi-aristeromycin.  An unusual directive effect in hydroxylations

Section: Bishydroxylationmentioning

confidence: 99%

Synthesis and Anti-HIV Activity of Novel 4'-Ethyl-5'-norcarbocyclic Adenosine Phosphonic Acid Analogues

Yoo¹,

Li²,

Lee³

et al. 2010

“…19 A complete NOE study allowed an unambiguous determination of their respective stereochemistry (Fig. 2).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Some Properties of 4'-Phenyl-5'-Norcarbocyclic Adenosine Phosphonic Acid Analogues

Liu¹,

Kim²,

Hong

2011

Steric and electronic parameters of 4'-substituents play significant roles in steering the conformation of nucleoside analogues. In order to investigate the relationship of 4'-substituent with antiviral enhancement, novel 4'-phenyl-5'-norcarbocyclic adenosine phosphonic acid analogues were racemically synthesized via de novo acyclic stereoselective route from propionaldehyde 5. The phenyl substituted cyclopentenols 15a and 15b as key intermediates were successfully constructed via reiterative carbonyl addition of Grignard reagents and ring-closing metathesis of corresponding divinyl 14. The synthesized nucleoside phosphonic acids analogues 19, 20, 21, and 23 were subjected to antiviral screening against HIV-1.

“…For the synthesis of nucleoside phosphonate by alkylation of the oxygen at C4 of (14), the silyl protection was removed. Further treatment of the nucleoside (15) with diisopropylphosphonomethyl bromide yielded the desired compound (16); the chlorine group of (16) was then transformed to amine with methanolic ammonia in a steel bomb to give adenine derivative (17).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anti-HCV Activity of 3',5'-cyclic SATE Phosphonodiester Nucleoside as a Novel Prodrug

Liu¹,

Seo²,

Yoo³

et al. 2010

A novel 2',4'-dimethyl carbocyclic adenosine 5'-phosphonic acid analogue (20) was prepared using acyclic stereoselective route from commercially available 4-hydroxybutan-2-one (4). To improve cellular permeability and enhance the anti-HCV activity of this phosphonic acid, a 3',5'-cyclic SATE phosphonodiester nucleoside prodrug (22) was prepared. The synthesized phosphonic nucleoside analogues, (20) and (22), were assayed for their ability to inhibit HCV RNA replication in a subgenomic replicon Huh7 cell line.