7 research outputs found
Synthesis of Protected 3âDeoxy-3-fluoro- and 4âDeoxy-4-fluoroâdâgalactopyranosides from Levoglucosan
Fluorinated carbohydrates are invaluable
tools to study various
biochemical processes. Herein, we describe a new strategy to access
orthogonally protected 3-deoxy-3-fluorogalactopyranose and acetylated
4-deoxy-4-fluorogalactopyranose. Starting from inexpensive levoglucosan,
most reactions were performed on a gram scale and allowed excellent
regio- and stereocontrol with a minimal use of protection/deprotection
cycles. Hence, we developed practical alternatives to the decade-long
reported method to access both 3-deoxy-3-fluoro- and 4-deoxy-4-fluorogalactopyranose
Palladium-Catalyzed Ullmann-Type Reductive Homocoupling of Iodoaryl Glycosides
A catalytic synthesis of novel biaryl-linked divalent
glycosides
was achieved using an electroreductive palladium-catalyzed iodoarylâiodoaryl
coupling reaction. This new method was optimized for the synthesis
of divalent biaryl-linked mannopyranosides that was subsequently generalized
toward several carbohydrate substrates with yields up to 96%
Synthesis and Biological Evaluation of Epidithioâ, Epitetrathioâ, and bis-(Methylthio)diketopiperazines: Synthetic Methodology, Enantioselective Total Synthesis of Epicoccin G, 8,8â˛-<i>epi</i>-<i>ent</i>-Rostratin B, Gliotoxin, Gliotoxin G, Emethallicin E, and Haematocin and Discovery of New Antiviral and Antimalarial Agents
An improved sulfenylation method for the preparation
of epidithio-,
epitetrathio-, and bis-(methylthio)Âdiketopiperazines from diketopiperazines
has been developed. Employing NaHMDS and related bases and elemental
sulfur or bisÂ[bisÂ(trimethylsilyl)Âamino]Âtrisulfide (<b>23</b>) in THF, the developed method was applied to the synthesis of a
series of natural and designed molecules, including epicoccin G (<b>1</b>), 8,8â˛-<i>epi</i>-<i>ent</i>-rostratin
B (<b>2</b>), gliotoxin (<b>3</b>), gliotoxin G (<b>4</b>), emethallicin E (<b>5</b>), and haematocin (<b>6</b>). Biological screening of selected synthesized compounds
led to the discovery of a number of nanomolar antipoliovirus agents
(i.e., <b>46</b>, 2,2â˛-<i>epi</i>-<b>46</b>, and <b>61</b>) and several low-micromolar anti-Plasmodium falciparum lead compounds (i.e., <b>46</b>, 2,2â˛-<i>epi</i>-<b>46</b>, <b>58</b>, <b>61</b>, and <b>1</b>)
Synthesis and Biological Evaluation of Epidithioâ, Epitetrathioâ, and bis-(Methylthio)diketopiperazines: Synthetic Methodology, Enantioselective Total Synthesis of Epicoccin G, 8,8â˛-<i>epi</i>-<i>ent</i>-Rostratin B, Gliotoxin, Gliotoxin G, Emethallicin E, and Haematocin and Discovery of New Antiviral and Antimalarial Agents
An improved sulfenylation method for the preparation
of epidithio-,
epitetrathio-, and bis-(methylthio)Âdiketopiperazines from diketopiperazines
has been developed. Employing NaHMDS and related bases and elemental
sulfur or bisÂ[bisÂ(trimethylsilyl)Âamino]Âtrisulfide (<b>23</b>) in THF, the developed method was applied to the synthesis of a
series of natural and designed molecules, including epicoccin G (<b>1</b>), 8,8â˛-<i>epi</i>-<i>ent</i>-rostratin
B (<b>2</b>), gliotoxin (<b>3</b>), gliotoxin G (<b>4</b>), emethallicin E (<b>5</b>), and haematocin (<b>6</b>). Biological screening of selected synthesized compounds
led to the discovery of a number of nanomolar antipoliovirus agents
(i.e., <b>46</b>, 2,2â˛-<i>epi</i>-<b>46</b>, and <b>61</b>) and several low-micromolar anti-Plasmodium falciparum lead compounds (i.e., <b>46</b>, 2,2â˛-<i>epi</i>-<b>46</b>, <b>58</b>, <b>61</b>, and <b>1</b>)
Synthesis and Biological Evaluation of Epidithioâ, Epitetrathioâ, and bis-(Methylthio)diketopiperazines: Synthetic Methodology, Enantioselective Total Synthesis of Epicoccin G, 8,8â˛-<i>epi</i>-<i>ent</i>-Rostratin B, Gliotoxin, Gliotoxin G, Emethallicin E, and Haematocin and Discovery of New Antiviral and Antimalarial Agents
An improved sulfenylation method for the preparation
of epidithio-,
epitetrathio-, and bis-(methylthio)Âdiketopiperazines from diketopiperazines
has been developed. Employing NaHMDS and related bases and elemental
sulfur or bisÂ[bisÂ(trimethylsilyl)Âamino]Âtrisulfide (<b>23</b>) in THF, the developed method was applied to the synthesis of a
series of natural and designed molecules, including epicoccin G (<b>1</b>), 8,8â˛-<i>epi</i>-<i>ent</i>-rostratin
B (<b>2</b>), gliotoxin (<b>3</b>), gliotoxin G (<b>4</b>), emethallicin E (<b>5</b>), and haematocin (<b>6</b>). Biological screening of selected synthesized compounds
led to the discovery of a number of nanomolar antipoliovirus agents
(i.e., <b>46</b>, 2,2â˛-<i>epi</i>-<b>46</b>, and <b>61</b>) and several low-micromolar anti-Plasmodium falciparum lead compounds (i.e., <b>46</b>, 2,2â˛-<i>epi</i>-<b>46</b>, <b>58</b>, <b>61</b>, and <b>1</b>)
Synthesis and Biological Evaluation of Epidithioâ, Epitetrathioâ, and bis-(Methylthio)diketopiperazines: Synthetic Methodology, Enantioselective Total Synthesis of Epicoccin G, 8,8â˛-<i>epi</i>-<i>ent</i>-Rostratin B, Gliotoxin, Gliotoxin G, Emethallicin E, and Haematocin and Discovery of New Antiviral and Antimalarial Agents
An improved sulfenylation method for the preparation
of epidithio-,
epitetrathio-, and bis-(methylthio)Âdiketopiperazines from diketopiperazines
has been developed. Employing NaHMDS and related bases and elemental
sulfur or bisÂ[bisÂ(trimethylsilyl)Âamino]Âtrisulfide (<b>23</b>) in THF, the developed method was applied to the synthesis of a
series of natural and designed molecules, including epicoccin G (<b>1</b>), 8,8â˛-<i>epi</i>-<i>ent</i>-rostratin
B (<b>2</b>), gliotoxin (<b>3</b>), gliotoxin G (<b>4</b>), emethallicin E (<b>5</b>), and haematocin (<b>6</b>). Biological screening of selected synthesized compounds
led to the discovery of a number of nanomolar antipoliovirus agents
(i.e., <b>46</b>, 2,2â˛-<i>epi</i>-<b>46</b>, and <b>61</b>) and several low-micromolar anti-Plasmodium falciparum lead compounds (i.e., <b>46</b>, 2,2â˛-<i>epi</i>-<b>46</b>, <b>58</b>, <b>61</b>, and <b>1</b>)
Synthesis and Biological Evaluation of Epidithioâ, Epitetrathioâ, and bis-(Methylthio)diketopiperazines: Synthetic Methodology, Enantioselective Total Synthesis of Epicoccin G, 8,8â˛-<i>epi</i>-<i>ent</i>-Rostratin B, Gliotoxin, Gliotoxin G, Emethallicin E, and Haematocin and Discovery of New Antiviral and Antimalarial Agents
An improved sulfenylation method for the preparation
of epidithio-,
epitetrathio-, and bis-(methylthio)Âdiketopiperazines from diketopiperazines
has been developed. Employing NaHMDS and related bases and elemental
sulfur or bisÂ[bisÂ(trimethylsilyl)Âamino]Âtrisulfide (<b>23</b>) in THF, the developed method was applied to the synthesis of a
series of natural and designed molecules, including epicoccin G (<b>1</b>), 8,8â˛-<i>epi</i>-<i>ent</i>-rostratin
B (<b>2</b>), gliotoxin (<b>3</b>), gliotoxin G (<b>4</b>), emethallicin E (<b>5</b>), and haematocin (<b>6</b>). Biological screening of selected synthesized compounds
led to the discovery of a number of nanomolar antipoliovirus agents
(i.e., <b>46</b>, 2,2â˛-<i>epi</i>-<b>46</b>, and <b>61</b>) and several low-micromolar anti-Plasmodium falciparum lead compounds (i.e., <b>46</b>, 2,2â˛-<i>epi</i>-<b>46</b>, <b>58</b>, <b>61</b>, and <b>1</b>)