Desymmetrization of 4-hydroxy-2,5-cyclohexadienones by radical cyclization: synthesis of optically pure γ-lactones

2010 ◽  
Vol 46 (5) ◽  
pp. 701-703 ◽  
Author(s):  
Rajesh Sunasee ◽  
Derrick L. J. Clive
Keyword(s):  
Radical Cyclization ◽  
Optically Pure

scholarly journals Expedient Access to Enantiopure Cyclopentanic Natural Products: Total Synthesis of (-)-Cyclonerodiol

2015 ◽  
Vol 10 (1) ◽  
pp. 1934578X1501000
Author(s):  
Carmen Pérez Morales ◽  
M. Mar Herrador ◽  
José F. Quílez del Moral ◽  
Alejandro F. Barrero
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Radical Cyclization ◽  
Formal Synthesis ◽  
Common Precursor ◽  
Enantiospecific Synthesis ◽  
Optically Pure

Following the principles of collective total synthesis, a number of natural products sharing an optically pure, multifunctional, cyclopentanic core were synthesized from a common precursor: plinol A (1). This intermediate was efficiently obtained in only four steps from (-)-linalool (2) using as the key step a Ti(III)-mediated diastereoselective radical cyclization. The feasibility of this approach was confirmed with the expedient enantiospecific synthesis of cyclonerodiol (3), and the formal synthesis of chocol G (4) and piperitone (5).

The 5-exo-trig radical cyclization reaction under reductive and oxidative conditions in the synthesis of optically pure GABA derivatives

Tetrahedron ◽  
2004 ◽  
Vol 60 (48) ◽  
pp. 10809-10815 ◽  
Author(s):  
Verónica Rodríguez ◽  
Mario Sánchez ◽  
Leticia Quintero ◽  
Fernando Sartillo-Piscil
Keyword(s):  
Radical Cyclization ◽  
Cyclization Reaction ◽  
Gaba Derivatives ◽  
Optically Pure

A Peptoid with Extended Shape in Water

2019 ◽  
Author(s):  
Jumpei Morimoto ◽  
Yasuhiro Fukuda ◽  
Takumu Watanabe ◽  
Daisuke Kuroda ◽  
Kouhei Tsumoto ◽  
...  
Keyword(s):  
Spectroscopic Analysis ◽  
Dimensional Space ◽  
Three Dimensional ◽  
Biomolecular Recognition ◽  
Biological Application ◽  
New Class ◽  
Proteolytic Resistance ◽  
Pharmacokinetic Properties ◽  
Optically Pure ◽  
Three Dimensional Space

<div> <div> <div> <p>“Peptoids” was proposed, over decades ago, as a term describing analogs of peptides that exhibit better physicochemical and pharmacokinetic properties than peptides. Oligo-(N-substituted glycines) (oligo-NSG) was previously proposed as a peptoid due to its high proteolytic resistance and membrane permeability. However, oligo-NSG is conformationally flexible and is difficult to achieve a defined shape in water. This conformational flexibility is severely limiting biological application of oligo-NSG. Here, we propose oligo-(N-substituted alanines) (oligo-NSA) as a new peptoid that forms a defined shape in water. A synthetic method established in this study enabled the first isolation and conformational study of optically pure oligo-NSA. Computational simulations, crystallographic studies and spectroscopic analysis demonstrated the well-defined extended shape of oligo-NSA realized by backbone steric effects. The new class of peptoid achieves the constrained conformation without any assistance of N-substituents and serves as an ideal scaffold for displaying functional groups in well-defined three-dimensional space, which leads to effective biomolecular recognition. </p> </div> </div> </div>

Fluoride-Catalyzed Addition of PhSCF2SiMe3toN-Substituted Cyclic Imides Followed by Radical Cyclization: General Synthetic Strategy ofgem-Difluoromethylenated 1-Azabicyclic Compounds

2009 ◽  
Vol 74 (10) ◽  
pp. 3798-3805 ◽  
Author(s):  
Teerawut Bootwicha ◽  
Duanghathai Panichakul ◽  
Chutima Kuhakarn ◽  
Samran Prabpai ◽  
Palangpon Kongsaeree ◽  
...  
Keyword(s):  
Radical Cyclization ◽  
Synthetic Strategy ◽  
Cyclic Imides ◽  
Azabicyclic Compounds
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