scholarly journals An invocation for computational evaluation of isomerization transforms: cationic skeletal reorganizations as a case study

2021 ◽  
Author(s):  
Alexander W. Schuppe ◽  
Yannan Liu ◽  
Timothy R. Newhouse
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Review Article ◽  
Computational Evaluation ◽  
Rearrangement Reactions ◽  
Cationic Rearrangement ◽  
The Many

This review article describes how cationic rearrangement reactions can be used in natural product total synthesis as a case study for the many productive ways by which isomerization reactions are enabling for synthesis.

scholarly journals Exploiting the Limits of Divergency Scaffolds in Natural Product Synthesis: The Case Study of Sesquiterpenoids

2021 ◽  
Author(s):  
Vera P. Demertzidou ◽  
Alexandros Zografos
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Rational Design ◽  
Natural Product Synthesis ◽  
Oxidation States

Divergent synthesis is a powerful but yet underdeveloped method to address the usual drawbacks of poor supply and confined diversity in the total synthesis of natural products. Herein, we describe the rational design behind the selection and the synthesis of a divergency scaffold for sesquiterpenoid lactones synthesis, as a case study, which provides access to a rich collection of carbocycles in different oxidation states within 8,12-sesquiterpenoids through simple, scalable transformations.

scholarly journals From Target-Oriented to Motif-Oriented: A Case Study on Nannocystin Total Synthesis

Molecules ◽  
2020 ◽  
Vol 25 (22) ◽  
pp. 5327
Author(s):  
Weicheng Zhang
Keyword(s):  
Drug Discovery ◽  
Total Synthesis ◽  
Natural Product ◽  
Chemical Space ◽  
Organic Transformations ◽  
Total Syntheses ◽  
Target Molecule ◽  
Structure Activity ◽  
Structural Diversification

Natural product total synthesis is in essence target-oriented in that a set of organic transformations are orchestrated into a workable process, leading ultimately to the target molecule with a predefined architecture. For a bioactive lead, proof of synthetic viability is merely the beginning. Ensuing effort repurposes the initial synthesis for structural diversification in order to probe structure-activity relationship (SAR). Yet accessibility is not equal to flexibility; moving from convergency to divergency, it is not always feasible to explore the chemical space around a particular substructure of interest simply by tweaking an established route. In this situation, the motif-oriented strategy becomes a superior choice, which gives priority to synthetic flexibility at the concerned site such that a route is adopted only if it is capable of implementing diversification therein. This strategy was recently devised by Fürstner et al., enabling them to achieve total synthesis of both natural and non-natural nannocystins varied at an otherwise challenging position. The present review examines seven distinctive nannocystin total syntheses reported thus far and showcases the merits of conventional (target-oriented) as well as motif-oriented strategies, concluding that these two approaches complement each other and are both indispensable for natural product based drug discovery.

Progress Toward The Total Synthesis Of The Marine Natural Product Karlotoxin 5

Planta Medica ◽  
2013 ◽  
Vol 79 (10) ◽  
Author(s):  
M Albadry ◽  
Y Zou ◽  
Y Takahashi ◽  
A Waters ◽  
M Hossein ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Marine Natural Product

Total Synthesis of the Antitumor Depsipeptide FE399 and its S-Benzyl Derivative: A Macrolactamization Approach

2020 ◽  
Author(s):  
Takayuki Tonoi ◽  
Miyuki Ikeda ◽  
Teruyuki Sato ◽  
Ryo Kawahara ◽  
Takatsugu Murata ◽  
...  
Keyword(s):  
Molecular Structure ◽  
Total Synthesis ◽  
Natural Product ◽  
Condensation Reaction ◽  
Practical Method ◽  
Equilibrium Mixture ◽  
Conformational Isomers ◽  
Single Isomer

<div>An efficient and practical method for the synthesis of (9R,14R,17R)-FE399, a novel antitumor bicyclic depsipeptide, was developed. A 2-methyl-6-nitrobenzoic anhydride (MNBA)-mediated dehydration condensation reaction was effectively employed for the formation of the 16-membered macrocyclic depsipeptide moiety of FE399. FE399 was found to exist as an inseparable equilibrium mixture of conformational isomers; the mixture was quantitatively transformed into the corresponding S-benzyl product and isolated as a single isomer. Thus, we could confirm that the molecular structure of FE399 obtained by this method is identical to that of the natural product.</div>

A One-Pot Chemoenzymatic Synthesis of (2S,4R)-4-Methylproline Enables the First Total Synthesis of Antiviral Lipopeptide Cavinafungin B

2018 ◽  
Author(s):  
Christian R. Zwick ◽  
Hans Renata
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Complex Molecule ◽  
Molecular Target ◽  
Chemoenzymatic Synthesis ◽  
General Strategy ◽  
One Pot

We report an efficient ten-step synthesis of antiviral natural product cavinafungin B in 37% overall yield. By leveraging a one-pot chemoenzymatic synthesis of (2S,4R)-4-methylproline and oxazolidine-tethered (Rink-Boc-ATG-resin) SPPS methodology, the assembly of our molecular target could be conducted in an efficient manner.This general strategy could prove amenable to the construction of other natural and unnatural linear lipopeptides. The value of incorporating biocatalytic steps in complex molecule synthesis is highlighted by this work.

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