scholarly journals Enantioselective Synthesis of the Predominant AB Ring System of the Schisandra Nortriterpenoid Natural Products

2014 ◽  
Vol 16 (17) ◽  
pp. 4480-4483 ◽  
Author(s):  
Birgit Gockel ◽  
Shermin S. Goh ◽  
Emma J. Puttock ◽  
Hannah Baars ◽  
Guilhem Chaubet ◽  
...  
Keyword(s):  
Natural Products ◽  
Ring System ◽  
Enantioselective Synthesis ◽  
Ab Ring

A concise enantioselective synthesis of the AB ring system of the manzamine alkaloids by ring-closing enyne metathesis

2001 ◽  
Vol 42 (18) ◽  
pp. 3235-3238 ◽  
Author(s):  
J.Stephen Clark ◽  
Robert J Townsend ◽  
Alexander J Blake ◽  
Simon J Teat ◽  
Amanda Johns
Keyword(s):  
Ring System ◽  
Enantioselective Synthesis ◽  
Enyne Metathesis ◽  
Manzamine Alkaloids ◽  
Ab Ring

Tungsten-Promoted Hetero-Pauson–Khand Cycloaddition: Application to the Total Synthesis of (–)-Allosecurinine

Synthesis ◽  
2019 ◽  
Vol 51 (09) ◽  
pp. 2001-2006 ◽  
Author(s):  
Egor Chirkin ◽  
Chouaha Bouzidi ◽  
François-Hugues Porée
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Intramolecular Cyclization ◽  
Late Stage ◽  
Ring System ◽  
Enantioselective Synthesis

Herein, we report a concise enantioselective synthesis of (–)-allosecurinine, a tetracyclic Securinega alkaloid featuring an α,β-unsaturated γ-lactone moiety. Starting from inexpensive and readily available trans-l-hydroxyproline, our strategy entails a rare late-stage [2+2+1]-hetero-Pauson–Khand cycloaddition between a ketone and an alkyne as the key complexity-generating step to rapidly install the CD-ring system. The reported W(CO)6-promoted intramolecular cyclization provides the first example of a tungsten-mediated hetero-Pauson–Khand reaction. This approach to the strained bicyclic CD motif present in ­allosecurinine provides some insights into the boundaries of this potentially powerful methodology that might be further extended to other butenolide-containing natural products.

ChemInform Abstract: A Concise Enantioselective Synthesis of the AB Ring System of the Manzamine Alkaloids by Ring-Closing Enyne Metathesis.

ChemInform ◽  
2010 ◽  
Vol 32 (29) ◽  
pp. no-no
Author(s):  
J. Stephen Clark ◽  
Robert J. Townsend ◽  
Alexander J. Blake ◽  
Simon J. Teat ◽  
Amanda Johns
Keyword(s):  
Ring System ◽  
Enantioselective Synthesis ◽  
Enyne Metathesis ◽  
Manzamine Alkaloids ◽  
Ab Ring

scholarly journals Studies toward the AB ring system of the tetrapetalone natural products

Tetrahedron ◽  
2015 ◽  
Vol 71 (35) ◽  
pp. 5886-5896 ◽  
Author(s):  
Peter N. Carlsen ◽  
Chao Jiang ◽  
Ildiko R. Herrick ◽  
Alison J. Frontier
Keyword(s):  
Natural Products ◽  
Ring System ◽  
Ab Ring

Synthesis of Spongidine A, D and Petrosaspongiolide L Methyl Ester Using Pyridine C-H Functionalization

2019 ◽  
Author(s):  
Florian Bartels ◽  
Manuela Weber ◽  
Mathias Christmann
Keyword(s):  
Natural Products ◽  
Methyl Ester ◽  
Hydrogen Atom ◽  
Phospholipase A2 ◽  
Late Stage ◽  
Hydrogen Atom Transfer ◽  
Ring System ◽  
Tetracyclic Core ◽  
Intramolecular Hydrogen ◽  
Phospholipase A2 Inhibitors

<div>An efficient strategy for the synthesis of the potent phospholipase A2 inhibitors spongidine A and D is presented. The tetracyclic core of the natural products was assembled via an intramolecular hydrogen atom transfer‐initiated Minisci reaction. A divergent late‐stage functionalization of the tetracyclic ring system was also used to achieve a concise synthesis of petrosaspongiolide L methyl ester.</div>

Enantioselective Syntheses of Flavonoid Diels-Alder Natural Products: A Review

2018 ◽  
Vol 15 (2) ◽  
pp. 221-229 ◽  
Author(s):  
Shah Bakhtiar Nasir ◽  
Noorsaadah Abd Rahman ◽  
Chin Fei Chee
Keyword(s):  
Natural Products ◽  
Organic Synthesis ◽  
Lewis Acid ◽  
Alder Reaction ◽  
Diels Alder ◽  
Enantioselective Synthesis ◽  
Chiral Ligand ◽  
Asymmetric Syntheses ◽  
Diels Alder Reaction ◽  
Enantioselective Syntheses

Background: The Diels-Alder reaction has been widely utilised in the syntheses of biologically important natural products over the years and continues to greatly impact modern synthetic methodology. Recent discovery of chiral organocatalysts, auxiliaries and ligands in organic synthesis has paved the way for their application in Diels-Alder chemistry with the goal to improve efficiency as well as stereochemistry. Objective: The review focuses on asymmetric syntheses of flavonoid Diels-Alder natural products that utilize chiral ligand-Lewis acid complexes through various illustrative examples. Conclusion: It is clear from the review that a significant amount of research has been done investigating various types of catalysts and chiral ligand-Lewis acid complexes for the enantioselective synthesis of flavonoid Diels-Alder natural products. The results have demonstrated improved yield and enantioselectivity. Much emphasis has been placed on the synthesis but important mechanistic work aimed at understanding the enantioselectivity has also been discussed.

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