Asymmetric Syntheses of (−)-8-epi-Swainsonine Triacetate and (+)-1,2-Di-epi-swainsonine. Carbonyl Addition Thwarted by an Unprecedented Aza-Pinacol Rearrangement

2000 ◽  
Vol 65 (18) ◽  
pp. 5693-5706 ◽  
Author(s):  
Hossein Razavi ◽  
Robin Polt
Keyword(s):  
Asymmetric Syntheses ◽  
Pinacol Rearrangement ◽  
Carbonyl Addition

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.

l-Prolinal Dithioacetal: A Highly Effective Organocatalyst for the Direct Nitro-Michael Addition to Selected Cyclic and Aromatic Ketones

Synthesis ◽  
2019 ◽  
Vol 51 (17) ◽  
pp. 3356-3368
Author(s):  
Piotr Pomarański ◽  
Zbigniew Czarnocki
Keyword(s):  
Michael Addition ◽  
Ring Size ◽  
Cyclic Ketones ◽  
Asymmetric Syntheses ◽  
Aromatic Ketones ◽  
Ring Systems ◽  
Effective Catalyst ◽  
Acetophenone Derivatives ◽  
Highly Effective ◽  
Related Compounds

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.

Concise asymmetric syntheses of streptazone A and abikoviromycin

2021 ◽  
Author(s):  
Gustav Wørmer ◽  
Nikolaj Villadsen ◽  
Peter Nørby ◽  
Thomas Bjørnskov Poulsen
Keyword(s):  
Asymmetric Syntheses

Using (+)-carvone to access novel derivatives of (+)-ent-cannabidiol: The first asymmetric syntheses of (+)-ent-CBDP and (+)-ent-CBDV

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

Enantio-complementary total asymmetric syntheses of prostaglandin E2 and prostaglandin F2?

1981 ◽  
pp. 1317 ◽  
Author(s):  
John Davies ◽  
Stanley M. Roberts ◽  
Derek P. Reynolds ◽  
Roger F. Newton
Keyword(s):  
Prostaglandin E2 ◽  
Asymmetric Syntheses
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