• Bulletin of the Korean Chemical Society
• /
• v.32 no.8
• /
• pp.2689-2694
• /
• 2011

Novel 5'-norcarbocyclic adenine and guanine phosphonic acid analogues with 6'-electronegative moiety such as unsaturated C-C bond were designed and synthesized from commercially available 2-methylene-propane-1,3-diol (4). Regioselective Mitsunobu reaction successfully proceeded from an allylic functional group (${\pm}$)-12b at low reaction temperature in polar cosolvent (DMF/1,4-dioxane) to give purine phosphonate analogues (${\pm}$)-13 and (${\pm}$)-20. The purine nucleoside phosphonate and phosphonic acid analogues were subjected to antiviral screening against HIV-1. Guanine analogue (${\pm}$)-23 shows significant anti-HIV activity in PBM cell lines ($EC_{50}=8.1\;{\mu}M$).

• Bulletin of the Korean Chemical Society
• /
• v.27 no.7
• /
• pp.976-980
• /
• 2006

The synthesis of 4'-phenyl and 1'-methyl doubly branched carbocyclic nucleoside was accomplished from 2-hydroxy acetophenone. The 4'-phenyl group was installed via a [3,3]-sigmatropic rearrangement reaction, and the carbonyl addition of methylmagnesium bromide was used to introduce the 1'-methyl group. Cyclization of divinyl 9 was performed using $2^{nd}$ generation Grubbs catalyst. The coupling of cyclopentenol 12$\alpha$ with 6-chloropurine by Mitsunobu reaction and desilylation was used to synthesize the target nucleoside 15.

• Bulletin of the Korean Chemical Society
• /
• v.23 no.1
• /
• pp.19-20
• /
• 2002

• Proceedings of the PSK Conference
• /
• 2003.10b
• /
• pp.186.4-187
• /
• 2003

Acanthoside-D, one of major components of Acanthopanacis Cortex, is known as a ginseng-like substance. it has been known to possess diverse biological effects. Acanthoside-D has a furofuran lignan structure and the synthesis of which poses interesting and often unsolved proplems of stereocontrol. Although a few interesting syntheses providing this natural product have been reported, an intermolecular McMurry coupling - intramolecular Mitsunobu cyclization route has not yet been explored. We report here a short and efficient synthetic pathway to the total synthesis of Acanthoside-D from aryl aldehydes and methyl acrylates via Baylis-Hillman reaction, intermolecular McMurry coupling and intramolecular Mitsunobu cyclization as key reaction.

• YAKHAK HOEJI
• /
• v.56 no.4
• /
• pp.230-235
• /
• 2012

Synthesis of novel cyclopropyl pyrimidine and purine nucleoside derivatives 2~8 with ${\alpha}$-configuration was successfully accomplished using an epoxide-ring opening reaction, lactonization, a hydroboration-oxidation reaction and a Mitsunobu reaction as the key steps. Antiviral activities against HSV-1 and -2, HIV-1 and -2, coxsackie B1and B3 viruses and poliovirus were assayed. Three compounds 4, 7 and 8 exhibit cytotoxicity-derived antiviral activity only in HIV-1 and -2.

• Bulletin of the Korean Chemical Society
• /
• v.30 no.9
• /
• pp.2039-2042
• /
• 2009

As a part of an ongoing effort to discover inhibitors of the Hepatitis C Virus RNA replication, we describe here the first synthetic route of 1'($\alpha$),2'($\beta$)-C-dimethyl carbocyclic adenine analogue. The key intermediate cyclopentenyl alcohol 8($\alpha$) was prepared from aldehyde 4 using ring-closing metathesis (RCM) as a key reaction. Coupling of 8($\alpha$) with nucleosidic base via the regioselective Mitsunobu reaction followed by stereoselective dihydoxylation and deprotection afforded the target carbocyclic adenine analogue 12.

• YAKHAK HOEJI
• /
• v.51 no.2
• /
• pp.103-107
• /
• 2007

In these study novel 1,4-disubstituted carbocyclic nucleoside analogues were synthesized as potential antiviral agents. The coupling reaction of the alcohol 8${\alpha}$ with natural bases using Mitsunobu reaction afforded the target nucleosides 13, 14. The synthesized compounds were evaluated for their antiviral activity against various viruses such as HIV-1, HSV-1, HSV-2 and HCMV. Cytosine derivative 13 exhibited moderate antiviral activity against HIV-1 (EC$_{50}$=16.4 ${\mu}$M).

• Bulletin of the Korean Chemical Society
• /
• v.31 no.9
• /
• pp.2514-2518
• /
• 2010

A very simple synthetic route of a novel SATE prodrug type of 6'-fluoro-6'-methyl-5'-noradeonosine carbocyclic nucleoside phosphonic acid is described. The key fluorinated alcohol intermediate 7 was prepared from the epoxide intermediate 6a via selective ring-opening of epoxide. Coupling of 7 with $N^6$-bis-Boc-adenine under a Mitsunobu reaction followed by phosphonation and deprotection afforded the carbocyclic phosphonic acid. The chemical stability of the bis(SATE) derivative 13 was measured at neutral (pH 7.2) and slightly acidic (Milli-Q water, pH 5.5) pH. The antiviral activity test of the SATE prodrug 13 and its parent nucleoside phosphonic acid 11 were evaluated against HIV-1.

• Bulletin of the Korean Chemical Society
• /
• v.29 no.8
• /
• pp.1447-1448
• /
• 2008

• Bulletin of the Korean Chemical Society
• /
• v.29 no.10
• /
• pp.1977-1982
• /
• 2008

Novel bicyclo[3.1.0]hexanyl purine nucleoside analogues were synthesized as potential antiherpetic agents via a bicyclo[3.1.0]hexanol (${\pm}$)-8, which was prepared using a highly efficient carbenoid cycloaddition reaction. A highly diastereoselective reduction of ketone and a Mitsunobu reaction for the condensation of glycosyl donor (${\pm}$)-12 with 6-chloropurine were employed.