Tellurium in organic synthesis: a new approach to trisubstituted γ-butyrolactones with trans–trans relative stereochemistry. Total enantioselective synthesis of (−)-Blastmycinolactol, (+)-Blastmycinone, (−)-NFX-2, and (+)-Antimycinone

2010 ◽  
Vol 51 (52) ◽  
pp. 6843-6846 ◽  
Author(s):  
Renan S. Ferrarini ◽  
Alcindo A. Dos Santos ◽  
João V. Comasseto
Keyword(s):  
Organic Synthesis ◽  
Enantioselective Synthesis ◽  
New Approach ◽  
Relative Stereochemistry

Zwitterionic Metal-Enolate or Equivalent: Generation and Capture

Synlett ◽  
2022 ◽  
Author(s):  
Linhong Zuo ◽  
Wusheng Guo
Keyword(s):  
Organic Synthesis ◽  
Building Blocks ◽  
Enantioselective Synthesis ◽  
New Approach ◽  
Material Chemistry

Functionalized ketones and their derivatives are very important building blocks in organic synthesis and material chemistry. The development of novel methodology for the chemo-, regio-, diastereo-, stereo- and enantioselective synthesis of functionalized ketones and their derivatives is the continuous endeavor of organic chemists. Herein we highlight the new approach that was recently initiated and developed by our group for the synthesis of (enantioenriched) ketones and related derivatives based on zwitterionic metal-enolate (ZME) chemistry.

Enantioselective Syntheses of Flavonoid Diels-Alder Natural Products: A Review

2018 ◽  
Vol 15 (2) ◽  
pp. 221-229 ◽  
Author(s):  
Shah Bakhtiar Nasir ◽  
Noorsaadah Abd Rahman ◽  
Chin Fei Chee
Keyword(s):  
Natural Products ◽  
Organic Synthesis ◽  
Lewis Acid ◽  
Alder Reaction ◽  
Diels Alder ◽  
Enantioselective Synthesis ◽  
Chiral Ligand ◽  
Asymmetric Syntheses ◽  
Diels Alder Reaction ◽  
Enantioselective Syntheses

Background: The Diels-Alder reaction has been widely utilised in the syntheses of biologically important natural products over the years and continues to greatly impact modern synthetic methodology. Recent discovery of chiral organocatalysts, auxiliaries and ligands in organic synthesis has paved the way for their application in Diels-Alder chemistry with the goal to improve efficiency as well as stereochemistry. Objective: The review focuses on asymmetric syntheses of flavonoid Diels-Alder natural products that utilize chiral ligand-Lewis acid complexes through various illustrative examples. Conclusion: It is clear from the review that a significant amount of research has been done investigating various types of catalysts and chiral ligand-Lewis acid complexes for the enantioselective synthesis of flavonoid Diels-Alder natural products. The results have demonstrated improved yield and enantioselectivity. Much emphasis has been placed on the synthesis but important mechanistic work aimed at understanding the enantioselectivity has also been discussed.

scholarly journals Learning from B12 enzymes: biomimetic and bioinspired catalysts for eco-friendly organic synthesis

2018 ◽  
Vol 14 ◽  
pp. 2553-2567 ◽  
Author(s):  
Keishiro Tahara ◽  
Ling Pan ◽  
Toshikazu Ono ◽  
Yoshio Hisaeda
Keyword(s):  
Organic Synthesis ◽  
Reaction Mechanisms ◽  
Catalytic Reactions ◽  
Vitamin B ◽  
Catalytic Systems ◽  
New Approach ◽  
Enzyme Functions

Cobalamins (B12) play various important roles in vivo. Most B12-dependent enzymes are divided into three main subfamilies: adenosylcobalamin-dependent isomerases, methylcobalamin-dependent methyltransferases, and dehalogenases. Mimicking these B12 enzyme functions under non-enzymatic conditions offers good understanding of their elaborate reaction mechanisms. Furthermore, bio-inspiration offers a new approach to catalytic design for green and eco-friendly molecular transformations. As part of a study based on vitamin B12 derivatives including heptamethyl cobyrinate perchlorate, we describe biomimetic and bioinspired catalytic reactions with B12 enzyme functions. The reactions are classified according to the corresponding three B12 enzyme subfamilies, with a focus on our recent development on electrochemical and photochemical catalytic systems. Other important reactions are also described, with a focus on radical-involved reactions in terms of organic synthesis.

Enantioselective synthesis of 1-aryl-2-propenylamines: a new approach to a stereoselective synthesis of the Taxol® side chain

2004 ◽  
Vol 15 (6) ◽  
pp. 941-949 ◽  
Author(s):  
Daniele Castagnolo ◽  
Silvia Armaroli ◽  
Federico Corelli ◽  
Maurizio Botta
Keyword(s):  
Stereoselective Synthesis ◽  
Enantioselective Synthesis ◽  
Side Chain ◽  
New Approach

scholarly journals Direct access to spirocycles by Pd/WingPhos-catalyzed enantioselective cycloaddition of 1,3-enynes

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Long Li ◽  
Shan Wang ◽  
Pengfei Luo ◽  
Ran Wang ◽  
Zheng Wang ◽  
...  
Keyword(s):  
Drug Discovery ◽  
Functional Groups ◽  
Organic Synthesis ◽  
Enantioselective Synthesis ◽  
Direct Access ◽  
Cycloaddition Reactions ◽  
Drug Discovery And Development ◽  
Spirocyclic Compounds ◽  
And Control ◽  
By Products

AbstractSpirocycles play an important role in drug discovery and development. The direct, catalytic, and enantioselective synthesis of spirocycles from readily available starting materials and in an atom economic manner remains a highly sought-after task in organic synthesis. Herein, an enantioselective Pd-hydride-catalyzed cycloaddition method for the synthesis of spirocyclic compounds directly from two classes of commonly available starting materials, 1,3-enynes and cyclic carbon−hydrogen (C−H) bonds, is reported. The reactions employ a chiral Pd/WingPhos catalyst to both suppress the formation of bis-allenyl by-products and control the stereoselectivity. 1,3-Enynes are used as dielectrophilic four-carbon units in the cycloaddition reactions, which also enables an enyne substrate-directed enantioselectivity switch with good levels of stereocontrol. The present spirocycle synthesis tolerates a broad range of functional groups of 1,3-enyne substrates, including alcohols, esters, nitriles, halides, and olefins. A variety of diverse cyclic nucleophiles, including pharmaceutically important heterocycles and carbocycles, can be flexibly incorporated with spiro scaffolds.

Thiol esters in organic synthesis. X. A new approach to 1,5-ketols and 5-hydroxy esters using S,S'-diethyl dithiomalonate as an ethanol carbanion equivalent

1982 ◽  
Vol 60 (1) ◽  
pp. 94-96 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Isaac V. Oppong
Keyword(s):  
Organic Synthesis ◽  
Raney Nickel ◽  
Michael Addition ◽  
New Approach ◽  
Unsaturated Esters ◽  
Thiol Esters ◽  
Hydroxy Esters

Michael addition of S,S′-diethyl dithiomalonate to conjugated enones and α,β-unsaturated esters followed by reduction with Raney nickel gave rise to 1,5-ketols and 5-hydroxy esters respectively in good yields.

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