Dienolates of Cycloalkenones and α,β-Unsaturated Esters Form Diels-Alder Adducts by a Michael/Michael-Tandem Reaction Rather Than in One Step

2018 ◽  
Vol 2019 (2-3) ◽  
pp. 562-573
Author(s):  
Ann-Christine Loesche ◽  
Reinhard Brückner
Keyword(s):  
Diels Alder ◽  
Tandem Reaction ◽  
Unsaturated Esters ◽  
One Step

scholarly journals Synthesis of fluorinated δ-lactams via cycloisomerization of gem-difluoropropargyl amides

2010 ◽  
Vol 6 ◽  
Author(s):  
Satoru Arimitsu ◽  
Gerald B Hammond
Keyword(s):  
Building Blocks ◽  
Alder Reaction ◽  
Diels Alder ◽  
Tandem Reaction ◽  
Enyne Metathesis ◽  
Metathesis Reaction ◽  
Ring Closing Metathesis ◽  
Diels Alder Reaction

gem-Difluoro-1,7-enyne amides are suitable building blocks for the synthesis of difluorodihydropyridinones via a ring-closing metathesis reaction, and of 4,4-difluoro-3-oxoisoquinolines through a ring-closing metathesis–enyne metathesis tandem reaction. These products, in turn, undergo a Diels–Alder reaction to yield heterotricyclic systems in moderate to good yields.

Copper(I)-Catalyzed Tandem Synthesis of 2-Acylquinolines from 2-Ethynylanilines and Glyoxals

2021 ◽  
Author(s):  
Guanghui Wang ◽  
Jian Jia ◽  
Gang Liu ◽  
mingwu Yu ◽  
Xiaoxiao Chu ◽  
...  
Keyword(s):  
Tandem Reaction ◽  
One Step ◽  
Tandem Synthesis

An efficient one-step synthesis of 2-acylquinolines by a copper-catalyzed tandem reaction of 2-ethynylanilines with glyoxals in the presence of piperidine has been developed. This new protocol successfully avoids the multi-step...

One-step Functionalization of Mildly and Strongly Reduced Graphene Oxide with Maleimide: An Experimental and Theoretical Investigation of the Diels-Alder [4+2] Cycloaddition Reaction

2021 ◽  
Author(s):  
Alfonso Ferretti ◽  
Sourab Sinha ◽  
Luca Sagresti ◽  
Esteban Araya-Hermosilla ◽  
Mirko Prato ◽  
...  
Keyword(s):  
Graphene Oxide ◽  
Reduced Graphene Oxide ◽  
Large Scale ◽  
Cycloaddition Reaction ◽  
Diels Alder ◽  
Reduced Form ◽  
Graphene Nanocomposites ◽  
Exfoliated Graphene ◽  
Reduced Graphene ◽  
One Step

For large-scale graphene applications, such as the production of polymer-graphene nanocomposites, exfoliated graphene oxide (GO) and its reduced form (rGO) are presently considered very suitable starting material, showing enhanced chemical...

The Roush Synthesis of ( + )-Superstolide A

2011 ◽  
Author(s):  
Douglass Taber
Keyword(s):  
Malignant Cell ◽  
Alder Reaction ◽  
Diels Alder ◽  
Protecting Group ◽  
The Third ◽  
Diels Alder Reaction ◽  
Single Diastereomer ◽  
Superstolide A ◽  
One Step ◽  
Fourth Component

( + )-Superstolide A 3, isolated from the New Caledonian sponge Neosiphonia superstes, shows interesting cytotoxicity against malignant cell lines at ~ 4 ng/mL concentration. The key transformation in the synthesis of 3 described (J. Am. Chem. Soc. 2008, 130, 2722) by William R. Roush of Scripps Florida was the transannular Diels-Alder cyclization of 2, which established, in one step with high diastereocontrol, both the cis decalin and the macrolactone of 3. The octaene 1 was assembled from four stereodefined fragments. The first, the linchpin 6, was prepared from the stannyl aldehyde 4. Homologation gave the enyne 5, which on hydroboration and oxidation gave 6. Earlier, Professor Roush had optimized the crotylation of the protected alaninal 7. In this case, the Brown reagent 8 delivered the desired Felkin product 9. Protection followed by ozonolysis gave the aldehyde 10. Crotylation with the Roush-developed tartrate 11 then gave the alkene 12, setting the stage for conversion to the iodide 13. Coupling of 13 with 6 completed the preparation of 14. The third component of (+)-superstolide A 3, the phosphonium salt 21, was assembled by Brown allylation of the aldehyde 15, to give 17. Protecting group interchange followed by ozonolysis delivered 18, which via Still-Gennari homologation was carried on to 21. Condensation with the fourth component, the aldehyde 22 , and esterification with 14 then gave 1. Under high dilution Suzuki conditions 1 was converted to 2. Storage in CDCl3 for five days, or brief warming, cyclized 2 to a single diastereomer of the transannular Diels-Alder product, that was carried on to (+)-superstolide A 3. While acyclic trienes comparable to 2 could be induced to cyclize, the transannular Diels-Alder reaction proceeded with much higher diastereocontrol.

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