Natural Product Biosynthesis Via the Diels-Alder Reaction

1992 ◽  
pp. 319-328 ◽  
Author(s):  
Robert D. Stipanovic
Keyword(s):  
Natural Product ◽  
Alder Reaction ◽  
Diels Alder ◽  
Natural Product Biosynthesis ◽  
Diels Alder Reaction

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 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 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).

scholarly journals Tandem Enyne Metathesis-Diels—Alder Reaction for Construction of Natural Product Frameworks.

ChemInform ◽  
2004 ◽  
Vol 35 (32) ◽  
Author(s):  
Marta Rosillo ◽  
Gema Dominguez ◽  
Luis Casarrubios ◽  
Ulises Amador ◽  
Javier Perez-Castells
Keyword(s):  
Natural Product ◽  
Alder Reaction ◽  
Diels Alder ◽  
Enyne Metathesis ◽  
Diels Alder Reaction

scholarly journals Studies towards the Synthesis of the Antibiotic Tetrodecamycin

Synlett ◽  
2018 ◽  
Vol 29 (08) ◽  
pp. 1117-1121
Author(s):  
Victor Lee ◽  
Jing He ◽  
Jack Baldwin
Keyword(s):  
Natural Product ◽  
Wittig Reaction ◽  
Alder Reaction ◽  
Membered Ring ◽  
Diels Alder ◽  
Acid Moiety ◽  
Tetronic Acid ◽  
Diels Alder Reaction

A study towards the natural product tetrodecamycin is reported. A modified Schlosser–Wittig reaction was utilized to prepare the precursor for the subsequent intramolecular Diels–Alder reaction, which delivered the trans-decalin ring of the natural product. The tetronic­ acid moiety of the molecule was prepared by a Dieckmann cyclization­. The cyclization of the tetronic acid to the trans-decalin double­ bond to form a seven-membered ring was examined.

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