scholarly journals P(III) vs. P(V): A P(V) Reagent for Thiophosphoramidate Linkages and Application to An Asymmetric Synthesis of a Cyclic Dinucleotide STING Agonist

2021 ◽  
Author(s):  
Bin Zheng ◽  
Chao Hang ◽  
Jason Zhu ◽  
Geoffrey Purdum ◽  
Melda Sezen-Edmonds ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Functional Groups ◽  
Stereoselective Synthesis ◽  
Key Functional Groups ◽  
First Time ◽  
Cyclic Dinucleotide

A highly stereoselective synthesis of a cyclic dinucleotide (CDN) STING agonist containing two chiral thiophosphoramidate linkages is described. These rare, yet key functional groups were, for the first time, installed efficiently and with high diastereoselectivity using a specially designed P(V) reagent. By utilizing this strategy, the CDN was prepared in greater than sixteen-fold higher yield than the prior P(III) approach, with fewer hazardous reagents and chromatographic purifications.

scholarly journals P(III) vs. P(V): A P(V) Reagent for Thiophosphoramidate Linkages and Application to An Asymmetric Synthesis of a Cyclic Dinucleotide STING Agonist

2021 ◽  
Author(s):  
Bin Zheng ◽  
Chao Hang ◽  
Jason Zhu ◽  
Geoffrey Purdum ◽  
Melda Sezen-Edmonds ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Functional Groups ◽  
Stereoselective Synthesis ◽  
Key Functional Groups ◽  
First Time ◽  
Cyclic Dinucleotide

A highly stereoselective synthesis of a cyclic dinucleotide (CDN) STING agonist containing two chiral thiophosphoramidate linkages is described. These rare, yet key functional groups were, for the first time, installed efficiently and with high diastereoselectivity using a specially designed P(V) reagent. By utilizing this strategy, the CDN was prepared in greater than sixteen-fold higher yield than the prior P(III) approach, with fewer hazardous reagents and chromatographic purifications.

A phenanthroline-based porous organic polymer for the iridium-catalyzed hydrogenation of carbon dioxide to formate

2019 ◽  
Vol 7 (23) ◽  
pp. 14019-14026 ◽  
Author(s):  
Gunniya Hariyanandam Gunasekar ◽  
Sungho Yoon
Keyword(s):  
Carbon Dioxide ◽  
Functional Groups ◽  
Single Site ◽  
Organic Polymer ◽  
Selective Catalyst ◽  
Porous Organic Polymer ◽  
Highly Active ◽  
First Time ◽  
Hydrogenation Of Carbon Dioxide ◽  
Hydrogenation Of Co

A novel phenanthroline-functionalized porous organic polymer (phen-POP) has been designed, and prepared for the first time without other reactive functional groups in the polymer skeleton. Post-synthetic metalation of phen-POP with IrCl3 afforded a single-site, highly active and selective catalyst for the hydrogenation of CO2 to formate.

Stereoselective synthesis of an eleganine A core

2020 ◽  
Vol 18 (24) ◽  
pp. 4566-4568
Author(s):  
Gints Smits ◽  
Ronalds Zemribo
Keyword(s):  
Stereoselective Synthesis ◽  
Core Structure ◽  
The Core ◽  
First Time

The core structure of eleganine A – a cytotoxic indole monoterpene alkaloid – was accessed for the first time.

Electrochemical Synthesis of 2-Hydroxy-para-terphenyls by Dehydrogenative Anodic C–C Cross-Coupling Reaction

Synlett ◽  
2019 ◽  
Vol 30 (10) ◽  
pp. 1174-1177 ◽  
Author(s):  
Sebastian Lips ◽  
Robert Franke ◽  
Siegfried R. Waldvogel
Keyword(s):  
Functional Groups ◽  
Electrochemical Synthesis ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Cross Coupling Reaction ◽  
Wide Range ◽  
Broad Variety ◽  
First Time ◽  
Fast Access

The anodic C–C cross-coupling reaction provides fast access to a wide range of bi- and terarylic scaffolds by electrochemically mediated arylation reactions. Herein, a metal- and reagent-free electrosynthetic protocol for the synthesis of nonsymmetrical 2-hydroxy-para-teraryl derivatives is presented for the first time. It is scalable, easy to conduct, and allows the use of a broad variety of different functional groups.

scholarly journals Chiral Thioureas—Preparation and Significance in Asymmetric Synthesis and Medicinal Chemistry

Molecules ◽  
2020 ◽  
Vol 25 (2) ◽  
pp. 401 ◽  
Author(s):  
Franz Steppeler ◽  
Dominika Iwan ◽  
Elżbieta Wojaczyńska ◽  
Jacek Wojaczyński
Keyword(s):  
Hydrogen Bond ◽  
Drug Development ◽  
Asymmetric Synthesis ◽  
Stereoselective Synthesis ◽  
Strong Hydrogen Bond ◽  
Hydrogen Bond Donor ◽  
Drug Candidates ◽  
Current State ◽  
The Family ◽  
Donor Capability

For almost 20 years, thioureas have been experiencing a renaissance of interest with the emerged development of asymmetric organocatalysts. Due to their relatively high acidity and strong hydrogen bond donor capability, they differ significantly from ureas and offer, appropriately modified, great potential as organocatalysts, chelators, drug candidates, etc. The review focuses on the family of chiral thioureas, presenting an overview of the current state of knowledge on their synthesis and selected applications in stereoselective synthesis and drug development.

Towards the Total Synthesis of Schisandrene: Stereoselective Synthesis of the Dibenzocyclooctadiene Lignan Core

Synlett ◽  
2018 ◽  
Vol 29 (07) ◽  
pp. 908-911 ◽  
Author(s):  
K. Babu ◽  
Arramshetti Venkanna ◽  
Borra Poornima ◽  
Bandi Siva ◽  
B. Babu
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Asymmetric Reduction ◽  
Cross Coupling ◽  
Membered Ring ◽  
Stille Reaction ◽  
Reaction Sequence ◽  
Ring Closing Metathesis ◽  
Synthetic Strategy ◽  
First Time

A stereoselective synthesis of the dibenzocyclooctadiene ­lignan core of the natural product schisandrene is described. Starting from readily available gallic acid, the synthetic strategy involves Suzuki–Miyaura cross-coupling, Stille reaction, and ring-closing metathesis (RCM) in the reaction sequence. The required asymmetric center at C-7′ was established by an asymmetric reduction of a keto compound using the Corey–Bakshi–Shibata (CBS) catalyst. In our approach, the eight-membered ring was achieved by RCM for the first time.

Synthesis of phthalocyanine compounds bearing 2-(diethoxyphosphoryl)-4-methylpenta-1,3-dienyl functional groups

2013 ◽  
Vol 17 (05) ◽  
pp. 343-350 ◽  
Author(s):  
Alexander Yu. Tolbin ◽  
Victor E. Pushkarev ◽  
Irina O. Balashova ◽  
Valery K. Brel ◽  
Yuliana I. Gudkova ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Functional Groups ◽  
Spectroscopy Data ◽  
Free Base ◽  
Maldi Tof Mass Spectrometry ◽  
Maldi Tof ◽  
First Time

Free-base phthalocyanine ligands and their zinc derivatives representing functionally monosubstituted (A3B type) or tetrasubstituted (A4 type) compounds with 2-diethoxyphosphoryl-4-methylpenta-1,3-dienyl moieties have been synthesized for the first time. Their structures were characterized by MALDI-TOF mass-spectrometry as well as 1 H and 31 P NMR spectroscopy data. A tendency to aggregation in dependence on the nature of the solvent was demonstrated as well.

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