scholarly journals Facilitating Biomimetic Syntheses of Borrerine Derived Alkaloids by Means of Flow-Chemical Methods

2015 ◽  
Vol 68 (4) ◽  
pp. 693 ◽  
Author(s):  
Sonja B. Kamptmann ◽  
Steven V. Ley
Keyword(s):  
Natural Product ◽  
Flow Chemistry ◽  
Single Step ◽  
Natural Product Synthesis ◽  
Biomimetic Synthesis ◽  
Synthetic Chemistry ◽  
Chemical Methods ◽  
Complex Architectures

Flow chemistry is widely used nowadays in synthetic chemistry and has increasingly been applied to complex natural product synthesis. However, to date flow chemistry has not found a place in the area of biomimetic synthesis. Here we show the syntheses of borrerine derived alkaloids, indicating that we can use biomimetic principles in flow to prepare complex architectures in a single step.

scholarly journals All-carbon [3 + 2] cycloaddition in natural product synthesis

2020 ◽  
Vol 16 ◽  
pp. 3015-3031
Author(s):  
Zhuo Wang ◽  
Junyang Liu
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Structural Features ◽  
Single Step ◽  
Natural Product Synthesis ◽  
Synthetic Chemistry ◽  
Quaternary Centers ◽  
Chemical Structures ◽  
Quaternary Center ◽  
Medicinal Properties

Many natural products possess interesting medicinal properties that arise from their intriguing chemical structures. The highly-substituted carbocycle is one of the most common structural features in many structurally complicated natural products. However, the construction of highly-substituted, stereo-congested, five-membered carbocycles containing all-carbon quaternary center(s) is, at present, a distinct challenge in modern synthetic chemistry, which can be accessed through the all-carbon [3 + 2] cycloaddition. More importantly, the all-carbon [3 + 2] cycloaddition can forge vicinal all-carbon quaternary centers in a single step and has been demonstrated in the synthesis of complex natural products. In this review, we present the development of all-carbon [3 + 2] cycloadditions and illustrate their application in natural product synthesis reported in the last decade covering 2011–2020 (inclusive).

scholarly journals Advances in polycyclization cascades in natural product synthesis

2021 ◽  
Author(s):  
Yubo Jiang ◽  
Ryan E. McNamee ◽  
Philip J. Smith ◽  
Ana Sozanschi ◽  
Zixuan Tong ◽  
...  
Keyword(s):  
Natural Product ◽  
Cascade Reactions ◽  
Single Step ◽  
Natural Product Synthesis ◽  
Ring Systems ◽  
Recent Advances ◽  
Powerful Means ◽  
Multiple Ring

Cascade reactions are among the most powerful means to achieve the construction of multiple ring systems in a single step. This tutorial review describes recent advances in the use of polycyclization cascades in natural product synthesis.

Formation of tetrasubstituted C–C double bonds via olefin metathesis: challenges, catalysts, and applications in natural product synthesis

2018 ◽  
Vol 5 (3) ◽  
pp. 494-516 ◽  
Author(s):  
Nirmalya Mukherjee ◽  
Sebastian Planer ◽  
Karol Grela
Keyword(s):  
Transition Metal ◽  
Natural Product ◽  
Olefin Metathesis ◽  
Natural Product Synthesis ◽  
Synthetic Chemistry ◽  
Double Bonds ◽  
Bond Forming ◽  
Bond Forming Reactions ◽  
The Many

Among the many types of transition-metal-catalysed C–C bond forming reactions, olefin metathesis is without a doubt one of the most thriving fields in modern organic synthetic chemistry.

A Short Synthesis of (+)-Brefeldin C via Enantioselective Radical Hydroalkynylation

2019 ◽  
Author(s):  
Lars Gnägi ◽  
Severin Vital Martz ◽  
Daniel Meyer ◽  
Robin Marc Schärer ◽  
Philippe Renaud
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Oxidation State ◽  
Single Step ◽  
Radical Process ◽  
Target Molecule ◽  
Short Synthesis ◽  
The One

<div><div><div><div><p>A very concise total synthesis of (+)-brefeldin C starting from 2-furanylcyclopentene is described. This approach is based on an unprecedented enantioselective radical hydroalkynylation process to introduce the two cyclopentane stereocenters in a single step. The use of a furan substituent allows to achieve a high trans diastereoselectivity during the radical process and it contains the four carbon atoms C1–C4 of the natural product in an oxidation state closely related to the one of the target molecule. The eight-step synthesis require six product purifications and it provides (+)-brefeldin C in 18% overall yield.</p></div></div></div></div>

Recent applications of asymmetric organocatalytic annulation reactions in natural product synthesis

2021 ◽  
Author(s):  
Nengzhong Wang ◽  
Zugen Wu ◽  
Junjie Wang ◽  
Nisar Ullah ◽  
Yixin Lu
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Natural Products Synthesis

A comprehensive and updated summary of asymmetric organocatalytic annulation reactions is presented; in particular, the applications of these annulation strategies to natural products synthesis are highlighted.

scholarly journals The Synthesis of Conjugated Bis-Aryl Vinyl Substrates and Their Photoelectrocyclization Reactions towards Phenanthrene Derivatives

Synthesis ◽  
2021 ◽  
Author(s):  
Jon D. Rainier ◽  
Xuchen Zhao
Keyword(s):  
Natural Product ◽  
Natural Product Synthesis ◽  
Mechanistic Studies ◽  
Efficient Strategy

AbstractThe photoelectrocyclization of conjugated vinyl biaryls has proven to be a valuable and efficient strategy for generating phenanthrene derivatives. Contained in this review is an overview of the mechanism for the transformation and a discussion of the reaction scope with a focus on the electrocyclization itself, rearomatization, and the application of the reaction in natural product synthesis.1 Introduction2 The Synthesis of Conjugated Vinyl Biaryls3 Mechanistic Studies4 Substrate Scope5 Applications6 Conclusions

Palladium-catalyzed cascade cyclizations involving C–C and C–X bond formation: strategic applications in natural product synthesis

2021 ◽  
Author(s):  
K. R. Holman ◽  
A. M. Stanko ◽  
S. E. Reisman
Keyword(s):  
Natural Product ◽  
Bond Formation ◽  
Natural Product Synthesis ◽  
Cascade Cyclizations ◽  
Palladium Catalyzed ◽  
Multiple Rings

This tutorial review highlights the use of palladium-catalyzed cascade cyclizations in natural product synthesis, focusing on cascades that construct multiple rings and form both C–C and C–X (X = O, N) bonds in a single synthetic operation.

scholarly journals Applications of the Horner-Wadsworth-Emmons olefination in modern natural product synthesis

Synthesis ◽  
2021 ◽  
Author(s):  
Dávid Roman ◽  
Maria Sauer ◽  
Christine Beemelmanns
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Reaction Conditions ◽  
Comprehensive Review ◽  
Modern Natural ◽  
Key Steps ◽  
Synthetic Approaches

Here, we have summarized more than 30 representative natural product syntheses published in 2015 to 2020 that employ one or more Horner-Wadsworth-Emmons (HWE) reactions. We comprehensively describe the applied phosphonate reagents, HWE reaction conditions and key steps of the total synthetic approaches. Our comprehensive review will support future synthetic approaches and serve as guideline to find the best HWE conditions for the most complicated natural products known

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