Extensive methodology screening of meso-tetrakys-(furan-2-yl)-porphyrin microwave-assisted synthesis

2016 ◽  
Vol 40 (3) ◽  
pp. 2574-2581 ◽  
Author(s):  
Federica Bosca ◽  
Silvia Tagliapietra ◽  
Claudio Garino ◽  
Giancarlo Cravotto ◽  
Alessandro Barge
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Microwave Assisted Synthesis ◽  
Microwave Assisted ◽  
Diels Alder Reaction ◽  
One Step ◽  
Fast Procedure

meso-Tetrakys-(furan-2-yl)-porphyrin has been prepared by a one step, microwave assisted, fast procedure. The Diels–Alder reaction is proposed to further decorate the porphyrin scaffold.

Microwave-Assisted Synthesis of Camphor-Derived Chiral Imidazolium Ionic Liquids and Their Application in Diastereoselective Diels-Alder Reaction

Synthesis ◽  
2007 ◽  
Vol 2007 (9) ◽  
pp. 1333-1338 ◽  
Author(s):  
Peter Gaertner ◽  
Katharina Bica ◽  
Guenter Gmeiner ◽  
Christian Reichel ◽  
Bernhard Lendl
Keyword(s):  
Ionic Liquids ◽  
Alder Reaction ◽  
Diels Alder ◽  
Microwave Assisted Synthesis ◽  
Imidazolium Ionic Liquids ◽  
Microwave Assisted ◽  
Diels Alder Reaction

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.

One step synthesis of 2-alkenylchromanes via inverse electron-demand Hetero-Diels–Alder reaction of o -quinone methide with unactivated dienes

Tetrahedron ◽  
2016 ◽  
Vol 72 (47) ◽  
pp. 7642-7649 ◽  
Author(s):  
Jian Liu ◽  
Xiaoxiao Wang ◽  
Lubin Xu ◽  
Zhihui Hao ◽  
Liang Wang ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Quinone Methide ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
One Step ◽  
Electron Demand
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