Rapid construction of tetrahydropyridine scaffolds via formal imino Diels–Alder reactions of Schiff bases and Nazarov reagents

2019 ◽  
Vol 17 (39) ◽  
pp. 8827-8831 ◽  
Author(s):  
Yen-Ku Wu ◽  
Viresh H. Rawal
Keyword(s):  
Schiff Bases ◽  
Diels Alder ◽  
Protic Solvents ◽  
Rapid Construction

A collection of piperidine derivatives including tetrabenazine was synthesized via aza-annulation of Nazarov reagents and Schiff bases in protic solvents.

Intramolecular Diels–Alder reactions of the furan diene (IMDAF); rapid construction of highly functionalised isoquinoline skeletons

1995 ◽  
pp. 2393-2398 ◽  
Author(s):  
Tomas Hudlicky ◽  
Gabor Butora ◽  
Stephen P. Fearnley ◽  
Andrew G. Gum ◽  
P. J. Persichini ◽  
...  
Keyword(s):  
Diels Alder ◽  
Rapid Construction

Rapid Construction of Fold-Line-Shaped BN-Embedded Polycyclic Aromatic Compounds through Diels–Alder Reaction

2019 ◽  
Vol 85 (1) ◽  
pp. 241-247
Author(s):  
Peng-Fei Zhang ◽  
Fang-Dong Zhuang ◽  
Ze-Hao Sun ◽  
Yang Lu ◽  
Jie-Yu Wang ◽  
...  
Keyword(s):  
Aromatic Compounds ◽  
Alder Reaction ◽  
Diels Alder ◽  
Polycyclic Aromatic Compounds ◽  
Diels Alder Reaction ◽  
Fold Line ◽  
Rapid Construction ◽  
Polycyclic Aromatic

An approach towards the construction of the tetracyclic skeleton of palhinine alkaloids

2020 ◽  
Vol 7 (16) ◽  
pp. 2243-2246 ◽  
Author(s):  
Congcong Han ◽  
Yang Chen ◽  
Yin-Cheung Ching ◽  
Chi-Sing Lee ◽  
Shuzhong He
Keyword(s):  
Lewis Acid ◽  
Diels Alder ◽  
Cascade Process ◽  
Rapid Construction ◽  
Acid Catalyzed ◽  
Tetracyclic Core

A bifunctional Lewis acid catalyzed Diels–Alder/carbocyclization cascade process was developed for the rapid construction of the tetracyclic core of palhinine alkaloids.

ChemInform Abstract: Intramolecular Diels-Alder Reactions of the Furan Diene (IMDAF); Rapid Construction of Highly Functionalized Isoquinoline Skeletons.

ChemInform ◽  
2010 ◽  
Vol 27 (4) ◽  
pp. no-no
Author(s):  
T. HUDLICKY ◽  
G. BUTORA ◽  
S. P. FEARNLEY ◽  
A. G. GUM ◽  
P. J. III PERSICHINI ◽  
...  
Keyword(s):  
Diels Alder ◽  
Rapid Construction

scholarly journals Biomimetic approach to the catalytic enantioselective synthesis of tetracyclic isochroman

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Xiangfeng Lin ◽  
Xianghui Liu ◽  
Kai Wang ◽  
Qian Li ◽  
Yan Liu ◽  
...  
Keyword(s):  
Natural Products ◽  
Biosynthetic Pathway ◽  
Experimental Studies ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Rapid Construction ◽  
Stereoselective Method ◽  
Biomimetic Approach

AbstractPolyketide oligomers containing the structure of tetracyclic isochroman comprise a large class of natural products with diverse activity. However, a general and stereoselective method towards the rapid construction of this structure remains challenging due to the inherent instability and complex stereochemistry of polyketide. By mimicking the biosynthetic pathway of this structurally diverse set of natural products, we herein develop an asymmetric hetero-Diels–Alder reaction of in-situ generated isochromene and ortho-quinonemethide. A broad range of tetracyclic isochroman frameworks are prepared in good yields and excellent stereoinduction (up to 95% ee) from readily available α-propargyl benzyl alcohols and 2-(hydroxylmethyl) phenols under mild conditions. This direct enantioselective cascade reaction is achieved by a Au(I)/chiral Sc(III) bimetallic catalytic system. Experimental studies indicate that the key hetero-Diels-Alder reaction involves a stepwise pathway, and the steric hindrance between in-situ generated isochromene and t-Bu group of Sc(III)/N,N’-dioxide complex is responsible for the enantioselectivity in the hetero-Diels–Alder reaction step.

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