Stereoselective synthesis of 2,6-disubstituted piperidine alkaloids

2020 ◽  
Vol 18 (29) ◽  
pp. 5493-5512 ◽  
Author(s):  
Nikhil Srivastava ◽  
Lingamurthy Macha ◽  
Hyun-Joon Ha
Keyword(s):  
Natural Products ◽  
Stereoselective Synthesis ◽  
Synthetic Methods ◽  
Structural Motif ◽  
Piperidine Alkaloids ◽  
Stereochemical Control

The synthetic methods to build the 2,6-disubstituted piperidine structural motif were described focusing on stereochemical control of two substituents at C2 and C6 with specific examples of natural products.

Synthetic Approaches to 2,6-trans-Tetrahydropyrans

Synthesis ◽  
2017 ◽  
Vol 49 (22) ◽  
pp. 4899-4916 ◽  
Author(s):  
Rongbiao Tong ◽  
Zhihong Zhang
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Michael Addition ◽  
Synthetic Methods ◽  
Bioactive Molecules ◽  
Structural Motif ◽  
Heck Cyclization ◽  
Epoxide Opening ◽  
Oxocarbenium Ion ◽  
Synthetic Approaches

Being different from 2,6-cis-tetrahydropyrans (2,6-cis-THPs), the corresponding 2,6-trans-THPs are thermodynamically less stable and more challenging to construct. The fact that there are many natural products and/or bioactive molecules containing this 2,6-trans-THP subunit has led to the development of many efficient synthetic approaches to access 2,6-trans-THPs. This review summarizes various synthetic methods reported for this structural motif and/or related applications in the total synthesis of natural products.1 Introduction2 Nucleophilic Addition to an Oxocarbenium Ion (Strategy A)3 Intramolecular Oxa-Michael Addition (Strategy B)4 Intermolecular Michael Addition to Dihydropyranones (Strategy A)5 The Heck–Matsuda (Strategy A) Reaction and Oxa-Heck Cyclization (Strategy B)6 Intramolecular SN2 Substitution and Epoxide Opening (Strategy B)7 Miscellaneous Methods8 Conclusion and Outlook

scholarly journals Modern Synthetic Methods for the Stereoselective Construction of 1,3-Dienes

Molecules ◽  
2021 ◽  
Vol 26 (2) ◽  
pp. 249
Author(s):  
Raquel G. Soengas ◽  
Humberto Rodríguez-Solla
Keyword(s):  
Organic Chemistry ◽  
Natural Products ◽  
Functional Group ◽  
Biological Activities ◽  
Synthetic Methods ◽  
Bond Forming ◽  
Drug Candidates ◽  
The Past ◽  
Wide Range

The 1,3-butadiene motif is widely found in many natural products and drug candidates with relevant biological activities. Moreover, dienes are important targets for synthetic chemists, due to their ability to give access to a wide range of functional group transformations, including a broad range of C-C bond-forming processes. Therefore, the stereoselective preparation of dienes have attracted much attention over the past decades, and the search for new synthetic protocols continues unabated. The aim of this review is to give an overview of the diverse methodologies that have emerged in the last decade, with a focus on the synthetic processes that meet the requirements of efficiency and sustainability of modern organic chemistry.

Biosynthesis of cyclopropane in natural products

2022 ◽  
Author(s):  
Suze Ma ◽  
Dhanaraju Mandalapu ◽  
Shu Wang ◽  
Qi Zhang
Keyword(s):  
Natural Products ◽  
Biochemical Properties ◽  
Structural Motif ◽  
Enzymatic Pathways

This review discusses the diverse enzymatic pathways in the biosynthesis of cyclopropane, a unique structural motif with important biochemical properties.

Total Synthesis of the Pseudoindoxyl Class of Natural Products

2021 ◽  
Author(s):  
Pawan Surendra Dhote ◽  
Pitambar Patel ◽  
Kumar Vanka ◽  
Chepuri Ramana
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Structural Motif ◽  
Large Set

The pseudoindoxyl sub-structural motif, amongst the large set of the indole class of alkaloids, represents a unique subset of the oxygenated indole class of the alkaloids family. A majority of...

Asymmetric Hydrogenation of O-/N-Functional Group Substituted Arenes

2021 ◽  
Author(s):  
bingru shao ◽  
Lei Shi ◽  
Yong-Gui Zhou
Keyword(s):  
Natural Products ◽  
Functional Group ◽  
Asymmetric Hydrogenation ◽  
Biologically Active ◽  
Synthetic Methods

Asymmetric hydrogenation of aromatical compouds represents one of the most straightforward synthetic methods to construct important chiral cyclic skeletons that are often found in biologically active agents and natural products....

Beyond conventional construction of phthalimide core: A review

2021 ◽  
Author(s):  
Suven Das
Keyword(s):  
Natural Products ◽  
Organic Materials ◽  
Structural Motif ◽  
Primary Amines ◽  
Common Strategy ◽  
Phthalic Acids

Phthalimides are privileged structural motif frequently found in natural products, pharmaceuticals and organic materials. The Most common strategy for their synthesis involves condensation of phthalic acids/anhydrides with primary amines. However,...

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