Arabinosylamine in Asymmetric Syntheses of Chiral Piperidine Alkaloids

Synlett ◽  
2004 ◽  
pp. 671-674
Author(s):  
Horst Kunz ◽  
Birgit Kranke ◽  
Dominique Hebrault ◽  
Martin Schultz-Kukula
Synlett ◽  
2021 ◽  
Author(s):  
Gustav J. Wørmer ◽  
Thomas Bjørnskov Poulsen

Piperidine alkaloids continue to challenge the synthetic community by featuring densely functionalized scaffolds which often requires careful chemical orchestration. Streptazone A and abikoviromycin are small and highly functionalized piperidine alkaloids both accommodating Michael acceptors and a labile epoxide. These moieties are loaded into a [4.3.0] bicyclic core also present in other structurally related natural products including the well-known piperidine alkaloid streptazolin. Herein, we cover ring-closing strategies employed in prior streptazolin syntheses, provide a concise overview of structures, biological properties and biosyntheses of selected [4.3.0] piperidine alkaloids, and finally we disclose a complete coverage of our recent asymmetric syntheses of streptazone A and abikoviromycin.


ChemInform ◽  
2004 ◽  
Vol 35 (31) ◽  
Author(s):  
Birgit Kranke ◽  
Dominique Hebrault ◽  
Martin Schultz-Kukula ◽  
Horst Kunz

2018 ◽  
Vol 15 (2) ◽  
pp. 221-229 ◽  
Author(s):  
Shah Bakhtiar Nasir ◽  
Noorsaadah Abd Rahman ◽  
Chin Fei Chee

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.


Synthesis ◽  
2019 ◽  
Vol 51 (17) ◽  
pp. 3356-3368
Author(s):  
Piotr Pomarański ◽  
Zbigniew Czarnocki

The synthesis of novel l-prolinal dithioacetal and its application as an organocatalyst for the direct Michael addition of cyclic ketones and acetophenone derivatives to trans-β-nitrostyrene and related compounds is described. The prolinal dithioacetal acts as effective catalyst in the case of cyclic ketones of different ring size, in particular five- and six-membered examples, as well as larger and smaller ring systems. High enantioselectivity and diastereoselectivity is observed for different substrates and trans-β-nitrostyrenes. Also, the first asymmetric syntheses of selected 2-methyl-4-nitro-1,3-diphenylbutan-1-one derivatives by application of the obtained organocatalyst is presented.


Author(s):  
Gustav Wørmer ◽  
Nikolaj Villadsen ◽  
Peter Nørby ◽  
Thomas Bjørnskov Poulsen
Keyword(s):  

2021 ◽  
pp. 152891
Author(s):  
Alexandra E. Golliher ◽  
Antonio J. Tenorio ◽  
Nina O. Dimauro ◽  
Nicolas R. Mairata ◽  
F. Omar Holguin ◽  
...  

Author(s):  
John Davies ◽  
Stanley M. Roberts ◽  
Derek P. Reynolds ◽  
Roger F. Newton

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