Applications of chiral sulfoxides in enantioselective synthesis of diols and total synthesis of natural products

2002 ◽  
Vol 13 (5) ◽  
pp. 443-452 ◽  
Author(s):  
Guy Solladie
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Enantioselective Synthesis ◽  
Chiral Sulfoxides

scholarly journals Development of a Divergent Route to Erythrina Alkaloids

Synlett ◽  
2020 ◽  
Vol 31 (04) ◽  
pp. 327-333 ◽  
Author(s):  
Jesper L. Kristensen ◽  
Sebastian Clementson ◽  
Mikkel Jessing ◽  
Paulo J. Vital
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
19Th Century ◽  
First Generation ◽  
Second Generation ◽  
Enantioselective Synthesis ◽  
Third Generation ◽  
Synthetic Strategy ◽  
Erythrina Alkaloids ◽  
The 19Th Century

Erythrina alkaloids were identified at the end of the 19th century and today, more than 100 members of the erythrinane family have been isolated. They are characterized by a unique tetracyclic, α-tertiary spiroamine scaffold. Herein we detail our efforts towards the development of a divergent enantioselective synthesis of (+)-dihydro-β-erythroidine (DHβE) – one of the most prominent members of this intriguing family of natural products.1 Introduction2 Synthetic Strategy2.1 First Generation2.2 Second Generation2.3 Third Generation2.3.1 Radical Endgame2.3.2 Completion of the Total Synthesis3 Conclusion

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.

Pursuit of Enantioselective Synthesis of Heterocycle-Bearing ­Stereocenters: The Development of a Stereocontrolled BINOL-­Catalyzed Conjugate Addition of Organoboron Nucleophiles

Synlett ◽  
2017 ◽  
Vol 28 (16) ◽  
pp. 2093-2109 ◽  
Author(s):  
Jeremy May ◽  
Thien Nguyen ◽  
Truong Nguyen ◽  
Phong Le ◽  
Po-An Chen ◽  
...  
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Functional Groups ◽  
Conjugate Addition ◽  
Enantioselective Synthesis ◽  
Mechanistic Studies ◽  
Synthetic Strategy ◽  
Iterative Development

This account chronicles the iterative development of an enantioselective conjugate addition of organoboron nucleophiles to α,β-unsaturated enones and enals catalyzed by BINOL derivatives. Beginning with a specific application of this transformation to the total synthesis of the flinderole alkaloids, the transformation progressed to encompass a much larger scope of heterocycle-substituted electrophiles. The next phase saw progress toward the use of a broader scope of functional nucleophiles, with application in a strategy to synthesize discoipyrrole D. At each stage of this chronologically organized discussion, key problems, hypotheses, and solutions are presented to show the sources of discovery and solutions to problems as the catalyst and other reaction components were made more reactive. The interplay of target-directed reaction development, efforts to increase the scope of compatible functional groups, mechanistic studies, and empirical exploration is described to illustrate sources of chemical discovery.1 Introduction2 Synthesis of the Flinderole Natural Products3 Indole-Bearing Stereocenters4 Heteroaryl-Bearing Stereocenters5 Bis-Heteroaryl Stereocenters6 Synthetic Strategy for Discoipyrrole D7 Bis-Aryl Stereocenters8 Remaining Challenges9 Conclusion

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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