Insight into a natural Diels–Alder reaction from the structure of macrophomate synthase

Nature ◽  
2003 ◽  
Vol 422 (6928) ◽  
pp. 185-189 ◽  
Author(s):  
Toyoyuki Ose ◽  
Kenji Watanabe ◽  
Takashi Mie ◽  
Mamoru Honma ◽  
Hiromi Watanabe ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Insight Into

Deeper Insight into the Diels-Alder Reaction through the Activation Strain Model

2016 ◽  
Vol 11 (23) ◽  
pp. 3297-3304 ◽  
Author(s):  
Israel Fernández ◽  
F. Matthias Bickelhaupt
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Strain Model ◽  
Insight Into

Total Synthesis of Asperchalasine A

Synlett ◽  
2019 ◽  
Vol 31 (04) ◽  
pp. 301-308
Author(s):  
Jun Deng ◽  
Xianwen Long ◽  
Yiming Ding ◽  
Hai Wu
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Alder Reaction ◽  
Diels Alder ◽  
Oxidative Dearomatization ◽  
Diels Alder Reaction ◽  
Insight Into

Here we briefly reviewed recent synthetic progress toward cytochalasan trimer, asperchalasine A by Tang, Trauner and our group. This process features a highly stereoselective intermolecular Diels–Alder reaction and a HWE or RCM macrocyclization to establish the key monomer aspochalasin B. A late-stage biomimetic oxidative dearomatization of triphenol and subsequent [5+2] cycloaddition cascade furnished asperchalasine A. We anticipate that this key reaction could also be used for the synthesis of other merocytochalasans, and provide some insight into the biosynthetic connections of merocytochalasans. 1 Introduction2 Total Synthesis of Aspochalasin B 3 Total Synthesis of Asperchalasine A 4 Conclusions

scholarly journals Ab initio Study of Diels-Alder Reaction between Cyclic Dienes and Olefin

2021 ◽  
pp. 10-17
Author(s):  
Haydar A. Mohammad-Salim
Keyword(s):  
Organic Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Free Energies ◽  
Reaction Paths ◽  
Chemical Systems ◽  
Diels Alder Reaction ◽  
One Step ◽  
Step Mechanism ◽  
Insight Into

Theoretical modeling of organic synthesis is a powerful tool and leads to further insight into chemical systems. Computational chemistry allows obtaining the potential energy surface that experimentally cannot be observed, in addition to transition state calculations, which lead to better understanding the reactivity of an organic synthesis work. The Diels-Alder (DA) reaction of cyclopentadiene 1 and N-phenylmaleimide 2 has been studied at the MP2/6-311++G(d,p) level of theory. This DA reaction occurs through a one-step mechanism. It was expected that this reaction undergoes two regio-isomeric reaction paths passing through two different transition states to form two different products 3  and 4. The reaction paths are irreversible due to the exothermic character of -41.24 and -41.73 kcal.mol-1. This DA reaction are exergonic with reactions Gibbs free energies between -27.26 and -27.74 kcal⋅mol−1. Analysis of the CDFT indices predict the global electronic flux from the strong nucleophilic cyclopentadiene 1 to the electrophilic N-phenylmaleimide 2.

Mechanistic Insight into the Dehydro-Diels–Alder Reaction of Styrene–Ynes

2015 ◽  
Vol 80 (23) ◽  
pp. 11686-11698 ◽  
Author(s):  
Laura S. Kocsis ◽  
Husain N. Kagalwala ◽  
Sharlene Mutto ◽  
Bhaskar Godugu ◽  
Stefan Bernhard ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Mechanistic Insight ◽  
Insight Into

Insight into the informational-structure behavior of the Diels-Alder reaction of cyclopentadiene and maleic anhydride

2014 ◽  
Vol 20 (8) ◽  
Author(s):  
Moyocoyani Molina-Espíritu ◽  
Rodolfo O. Esquivel ◽  
Miroslav Kohout ◽  
Juan Carlos Angulo ◽  
José A. Dobado ◽  
...  
Keyword(s):  
Maleic Anhydride ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Insight Into

The Diels-Alder Reaction of 2-Ethenyl-1,4-Benzodioxin: A New and Simple Synthesis of Bisaryl Ethers

Synlett ◽  
1989 ◽  
Vol 1989 (01) ◽  
pp. 30-32
Author(s):  
Thomas V. Lee ◽  
Alistair J. Leigh ◽  
Christopher B. Chapleo
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Simple Synthesis ◽  
Diels Alder Reaction

The intermolecular anthracene-transfer in a regiospecific antipodal C60 difunctionalization

2020 ◽  
Author(s):  
Radu Talmazan ◽  
Klaus R. Liedl ◽  
Bernhard Kräutler ◽  
Maren Podewitz
Keyword(s):  
Noncovalent Interactions ◽  
Interaction Model ◽  
Alder Reaction ◽  
Diels Alder ◽  
Stacking Interactions ◽  
Pi Stacking ◽  
Diels Alder Reaction ◽  
Double Decker ◽  
Anthracene Molecule ◽  
New Strategies

We analyze the mechanism of the topochemically controlled difunctionalization of C60 and anthracene, where an anthracene molecule is transferred from one C60 monoadduct to another one under exclusive formation of equal amounts of C60 and the difficult to make antipodal C60 bisadduct. Our herein disclosed dispersion corrected DFT studies show the anthracene transfer to take place in a synchronous retro Diels-Alder/Diels-Alder reaction: an anthracene molecule dissociates from one fullerene under formation of an intermediate, while already undergoing stabilizing interactions with both neighboring fullerenes, facilitating the reaction kinetically. In the intermediate, a planar anthracene molecule is sandwiched between two neighboring fullerenes and forms equally strong "double-decker" type pi-pi stacking interactions with both of these fullerenes. Analysis with the distorsion interaction model shows that the anthracene unit of the intermediate is almost planar with minimal distorsions. This analysis sheds light on the existence of noncovalent interactions engaging both faces of a planar polyunsaturated ring and two convex fullerene surfaces in an unprecedented 'inverted sandwich' structure. Hence, it sheds light on new strategies to design functional fullerene based materials.<br>

Natural Products Biosynthesis Involving a Putative Diels-Alder Reaction

2016 ◽  
Vol 20 (22) ◽  
pp. 2421-2442 ◽  
Author(s):  
Kévin Cottet ◽  
Maria Kolympadi ◽  
Dean Markovic ◽  
Marie-Christine Lallemand
Keyword(s):  
Natural Products ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction
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