In Silico Design of Halogen-Bonding-Based Organocatalyst for Diels–Alder Reaction, Claisen Rearrangement, and Cope-Type Hydroamination

2016 ◽  
Vol 81 (17) ◽  
pp. 7459-7470 ◽  
Author(s):  
Choon Wee Kee ◽  
Ming Wah Wong
Keyword(s):  
In Silico ◽  
Claisen Rearrangement ◽  
Halogen Bonding ◽  
Alder Reaction ◽  
Diels Alder ◽  
In Silico Design ◽  
Diels Alder Reaction

Ring-Closing Metathesis Approach to Cage Propellanes Containing Oxepane and Tetrahydrofuran Hybrid System

Synthesis ◽  
2017 ◽  
Vol 49 (24) ◽  
pp. 5339-5350 ◽  
Author(s):  
Sambasivarao Kotha ◽  
Subba Cheekatla ◽  
Darshan Mhatre
Keyword(s):  
Claisen Rearrangement ◽  
Alder Reaction ◽  
Diels Alder ◽  
Ring Closing Metathesis ◽  
Cage Compounds ◽  
Transannular Cyclization ◽  
Diels Alder Reaction ◽  
Grignard Addition ◽  
Key Steps ◽  
First Time

The preparation of a variety of structurally interesting oxygenated cage compounds involving atom-economic processes such as Claisen rearrangement, Diels–Alder reaction, [2+2] photocycloaddition, and ring-closing metathesis (RCM) as key steps is reported. For the first time, oxepane ring system is introduced in cage framework using olefin metathesis as a key step. These cage systems assembled here are difficult to prepare by traditional methods. The synthetic sequence described here opens up new routes to higher order polycycles containing heteroatoms without the involvement of protecting groups. Transannular cyclization observed during Grignard addition and the RCM protocol used here may be applicable to generate unknown oxygenated cage systems.

scholarly journals Synthesis of a Biomimetic Tetracyclic Precursor of Aspochalasins Allowing a Formal Synthesis of Trichoderone A

2021 ◽  
Author(s):  
Oscar Gayraud ◽  
Benjamin Laroche ◽  
Nicolas Casaretto ◽  
Bastien Nay
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Alder Reaction ◽  
Diels Alder ◽  
Two Phase ◽  
Formal Synthesis ◽  
Diels Alder Reaction ◽  
Oxidative Transformations ◽  
High Degree

Aspochalasins are leucine-derived cytochalasins. Their complexity is often associated to a high degree of biosynthetic oxidative transformations that could inspire a two-phase strategy in total synthesis. In that context, we describe the synthesis of a putative biomimetic tetracyclic intermediate. The key constructive steps are an intramolecular Diels-Alder reaction to install the characteristic isoindolone core of cytochalasins, whose branched precursor was obtained from a stereoselective Ireland-Claisen rearrangement made on a highly unsaturated substrate. This work also constitutes a formal synthesis of trichoderone A.

scholarly journals A synthetic and in silico study on the highly regioselective Diels–Alder reaction of the polyenic antifungal antibiotics natamycin and flavofungin

2010 ◽  
Vol 51 (38) ◽  
pp. 4968-4971
Author(s):  
Zsolt Fejes ◽  
Attila Mándi ◽  
István Komáromi ◽  
László Majoros ◽  
Gyula Batta ◽  
...  
Keyword(s):  
In Silico ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Antifungal Antibiotics ◽  
In Silico Study

ChemInform Abstract: Application of the Novel Tandem Process Diels-Alder Reaction/Ireland-Claisen Rearrangement to the Synthesis of rac-Juvabione and rac-Epijuvabione.

ChemInform ◽  
2000 ◽  
Vol 31 (52) ◽  
pp. no-no
Author(s):  
Nicolas Soldermann ◽  
Joerg Velker ◽  
Olivier Vallat ◽  
Helen Stoeckli-Evans ◽  
Reinhard Neier
Keyword(s):  
Claisen Rearrangement ◽  
Alder Reaction ◽  
Diels Alder ◽  
The Novel ◽  
Diels Alder Reaction ◽  
Tandem Process
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