Diversity-oriented approach to natural product inspired pyrano-carbazole derivatives: strategic utilization of hetero-Diels–Alder reaction, Fischer indolization and the Suzuki–Miyaura cross-coupling reaction

Tetrahedron ◽  
2015 ◽  
Vol 71 (47) ◽  
pp. 9003-9011 ◽  
Author(s):  
Sambasivarao Kotha ◽  
Rashid Ali ◽  
Mohammad Saifuddin
Keyword(s):  
Natural Product ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Alder Reaction ◽  
Diels Alder ◽  
Carbazole Derivatives ◽  
Fischer Indolization ◽  
Diels Alder Reaction ◽  
Cross Coupling Reaction ◽  
Oriented Approach

Synthesis and Application of Tetrafluoroethylene (CF2CF2)-Containing Acetylene Derivatives

Synthesis ◽  
2020 ◽  
Vol 52 (13) ◽  
pp. 1947-1958
Author(s):  
Tsutomu Konno ◽  
Gen Egashira ◽  
Chihiro Kajimoto ◽  
Takuto Kataoka ◽  
Shigeyuki Yamada
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Alder Reaction ◽  
Diels Alder ◽  
Benzene Derivatives ◽  
Diels Alder Reaction ◽  
Cross Coupling Reaction ◽  
Oxidative Aromatization ◽  
High Yields ◽  
Acetylene Derivatives

On treating 1,3,4-tribromo-1,1,2,2-tetrafluorobutane, readily prepared from commercially available 4-bromo-3,3,4,4-tetrafluorobut-1-ene, with 3.3 equivalents of LHMDS at 0 °C in THF, the corresponding lithium acetylide could be prepared quantitatively. The acetylide reacted well with various aldehydes, ketones, or chlorosilanes to give the corresponding acetylene derivatives in high yields. It was also found that various iodoarenes could participate in the cross-coupling reaction with the zinc acetylide, readily prepared from the lithium acetylide and ZnCl2·TMEDA complex, in the presence of Pd(PPh3)4 to bring about the adducts in high yields. Thus-obtained acetylene derivatives underwent smooth Diels–Alder reaction with various 1,3-dienes to afford the corresponding 1,4- or 1,3-cyclohexadiene derivatives. In addition, it was revealed that the oxidative aromatization of the resulting cyclohexadiene derivatives with DDQ took place very smoothly, providing the multi-substituted benzene derivatives having a tetrafluoro­ethylene group.

scholarly journals Synthesis of 3,4-dihydro-1,8-naphthyridin-2(1H)-ones via microwave-activated inverse electron-demand Diels–Alder reactions

2014 ◽  
Vol 10 ◽  
pp. 282-286 ◽  
Author(s):  
Salah Fadel ◽  
Youssef Hajbi ◽  
Mostafa Khouili ◽  
Said Lazar ◽  
Franck Suzenet ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Alder Reaction ◽  
Diels Alder ◽  
Aryl Halides ◽  
Side Chain ◽  
Terminal Alkyne ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
Cross Coupling Reaction ◽  
Electron Demand

Substituted 3,4-dihydro-1,8-naphthyridin-2(1H)-ones have been synthesized with the inverse electron-demand Diels–Alder reaction from 1,2,4-triazines bearing an acylamino group with a terminal alkyne side chain. Alkynes were first subjected to the Sonogashira cross-coupling reaction with aryl halides, the product of which then underwent an intramolecular inverse electron-demand Diels–Alder reaction to yield 5-aryl-3,4-dihydro-1,8-naphthyridin-2(1H)-ones by an efficient synthetic route.

Asymmetric Synthesis of 3,3′-Piperidinoyl Spirooxindoles and Discovery of Stereospecific Cycloadducts as Novel Hedgehog Pathway Modulators

Synthesis ◽  
2020 ◽  
Vol 52 (21) ◽  
pp. 3140-3152
Author(s):  
Kamal Kumar ◽  
Mohammad Rehan ◽  
Jana Flegel ◽  
Franziska Heitkamp ◽  
Jorgelina L. Pergomet ◽  
...  
Keyword(s):  
Transition Metal ◽  
Small Molecules ◽  
Asymmetric Synthesis ◽  
Natural Product ◽  
Transition Metal Complexes ◽  
Alder Reaction ◽  
Diels Alder ◽  
Hedgehog Pathway ◽  
Diels Alder Reaction ◽  
Efficient Access

An enantioselective hetero-Diels–Alder reaction of alkylidene­ oxindoles and 2-aza-3-silyloxy-1,3-butadienes, catalyzed by divalent transition metal complexes with N,N′-dioxide ligands offered an efficient access to natural-product-based 3,3′-piperidinoyl spiroox­indole class of small molecules. exo-Cycloadducts formed via stereospecific cycloaddition with Z-olefin displayed potent activity in modulation of hedgehog pathway.

scholarly journals The Total Synthesis of (–)-Scabrolide a

2020 ◽  
Author(s):  
Nicholas Hafeman ◽  
Steven A. Loskot ◽  
Chris Reimann ◽  
Beau P. Pritchett ◽  
Scott C. Virgil ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

The first total synthesis of the norcembranoid diterpenoid scabrolide A is disclosed. The route begins with the synthesis of two chiral pool-derived fragments, which undergo a convergent coupling to expediently introduce all 19 carbon atoms of the natural product. An intramolecular Diels–Alder reaction and an enone-olefin cycloaddition/fragmentation sequence are then employed to construct the fused [5–6–7] linear carbocyclic core of the molecule and to complete the total synthesis.

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