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

ChemInform Abstract: The Novel Sequence Diels-Alder Reaction/Ireland-Claisen Rearrangement Applied to Acyclic Dienophiles: New Insights into the Selectivity of the Ireland-Claisen Rearrangement.

ChemInform ◽  
2010 ◽  
Vol 30 (44) ◽  
pp. no-no
Author(s):  
Joerg Velker ◽  
Jean-Philippe Roblin ◽  
Antonia Neels ◽  
Ana Tesouro ◽  
Helen Stoeckli-Evans ◽  
...  
Keyword(s):  
Claisen Rearrangement ◽  
Alder Reaction ◽  
Diels Alder ◽  
The Novel ◽  
Diels Alder Reaction

scholarly journals The Novel Sequence Diels-Alder Reaction/Ireland-Claisen Rearrangement Applied to Acyclic Dienophiles: New Insights into the Selectivity of the Ireland-Claisen Rearrangement

Synlett ◽  
1999 ◽  
Vol 1999 (Sup. 1) ◽  
pp. 925-929 ◽  
Author(s):  
Jörg Velker ◽  
Jean Philippe Roblin ◽  
Antonia Neels ◽  
Ana Tesouro ◽  
Helen Stoeckli-Evans ◽  
...  
Keyword(s):  
Claisen Rearrangement ◽  
Alder Reaction ◽  
Diels Alder ◽  
The Novel ◽  
Diels Alder Reaction

Synthese neuer Pyridin-C-nukleoside der 2 ,3 -Didesoxyribose durch „inverse“ [4+2]-Cycloaddition Synthesis of Novel Pyridine-C-nucleosides of 2,3-Dideoxyribose by „Inverse“ [4+2]-Cycloaddition

1997 ◽  
Vol 52 (7) ◽  
pp. 851-858 ◽  
Author(s):  
Gunther Seitz ◽  
Johanna Siegl
Keyword(s):  
Cycloaddition Reaction ◽  
Alder Reaction ◽  
Diels Alder ◽  
The Novel ◽  
Protecting Group ◽  
Enol Ethers ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
Cyclic Ketene Acetals

The anomeric imido esters 5 and 6, appropriate precursors for C-nucleoside synthesis, were prepared and utilized as heterodienophiles in a Diels-Alder reaction with inverse electron demand to yield the novel, protected 1.2.4-triazine C-nucleosides 8 and 9. They could be deprotected by treatment with 70% trifluoroacetic acid to furnish the free C-nucleosides 10 and 11. The triazine „aglycon“ of 8 contains an electron deficient diazadiene system, highly activated to react with various electron rich dienophiles such as enamines, enol ethers and several cyclic ketene acetals in an „inverse“ [4+2]-cycloaddition reaction. The Diels-Alder adducts spontaneously eliminate N2 and after follow-up reactions the O-TBDPS protected pyridine-C-nucleosides 13, 15, 17,19, 21 and 23 are formed. Removal of the protecting group by treatment with CF3CO2H /H2O leads to the corresponding 2’,3’-dideoxy-β-D-ribofuranosyl- pyridines.

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.

Asymmetric synthesis and the novel retro Diels–Alder reaction of a P -chiral sulfonyl-substituted phosphanorbornene

2000 ◽  
Vol 11 (13) ◽  
pp. 2661-2664 ◽  
Author(s):  
Pak-Hing Leung ◽  
Huifang Lang ◽  
Xiawei Zhang ◽  
S Selvaratnam ◽  
Jagadese J Vittal
Keyword(s):  
Asymmetric Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
The Novel ◽  
Diels Alder Reaction

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.

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