Evolution of Natural Product Scaffolds by Acyl- and Arylnitroso Hetero-Diels−Alder Reactions: New Chemistry on Piperine

2008 ◽  
Vol 73 (12) ◽  
pp. 4559-4567 ◽  
Author(s):  
Viktor Krchňák ◽  
Katherine R. Waring ◽  
Bruce C. Noll ◽  
Ute Moellmann ◽  
Hans-Martin Dahse ◽  
...  
Keyword(s):  
Natural Product ◽  
Diels Alder

scholarly journals Bispericyclic Diels–Alder Dimerization of ortho‐Quinols in Natural Product (Bio)Synthesis – Bioinspired Chemical 6‐Step Synthesis of (+)‐Maytenone

2021 ◽  
Author(s):  
Philippe A. Peixoto ◽  
Mourad El Assal ◽  
Isabelle Chataigner ◽  
Frédéric Castet ◽  
Anaëlle Cornu ◽  
...  
Keyword(s):  
Natural Product ◽  
Diels Alder ◽  
Bio Synthesis

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.

Diels-Alder Cascades in Natural Product Total Synthesis

2018 ◽  
pp. 159-189
Author(s):  
Richard P. Hsung ◽  
Zhi-Xiong Ma ◽  
Lichao Fang ◽  
John B. Feltenberger
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Diels Alder

Diels–Alder reaction of two green chiral precursors. Approach to natural product like structures

2016 ◽  
Vol 57 (43) ◽  
pp. 4791-4794 ◽  
Author(s):  
Gonzalo Carrau ◽  
Nicolas Veiga ◽  
Leopoldo Suescun ◽  
Germán F. Giri ◽  
Alejandra G. Suárez ◽  
...  
Keyword(s):  
Natural Product ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

scholarly journals Natural Product-Derived Modulators of Cell Cycle Progression and Viral Entry by Enantioselective Oxa Diels-Alder Reactions on the Solid Phase

2007 ◽  
Vol 14 (4) ◽  
pp. 443-451 ◽  
Author(s):  
Torben Leßmann ◽  
Michele G. Leuenberger ◽  
Sascha Menninger ◽  
Meritxell Lopez-Canet ◽  
Oliver Müller ◽  
...  
Keyword(s):  
Cell Cycle ◽  
Natural Product ◽  
Viral Entry ◽  
Cell Cycle Progression ◽  
Solid Phase ◽  
Diels Alder ◽  
Cycle Progression

scholarly journals Synthesis of a Novel Bicyclic Scaffold Inspired by the Antifungal Natural Product Sordarin

2018 ◽  
Author(s):  
Yibiao Wu ◽  
Chris Dockendorff
Keyword(s):  
Carboxylic Acid ◽  
Natural Product ◽  
Elongation Factor ◽  
Alder Reaction ◽  
Diels Alder ◽  
High Affinity ◽  
Diels Alder Reaction ◽  
Elongation Factor 2 ◽  
Eukaryotic Elongation Factor 2 ◽  
Eukaryotic Elongation Factor

A simplified bicyclic scaffold inspired by the antifungal natural product sordarin was designed and synthesized which maintains the carboxylic acid/aldehyde (or nitrile) pharmacophore. A densely functionalized chiral cyclopentadiene was constructed in 8 steps and utilized in a Diels-Alder reaction with acrylonitrile. The resulting [2.2.1]cycloheptene was transformed into a scaffold possessing vicinal carboxylic acid and nitrile groups, with orientations predicted to provide high affinity for the fungal protein eukaryotic elongation factor 2 (eEF2).

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