Total Synthesis of Complex Natural Products: Combination of Chemical Synthesis and Biosynthesis Strategies

2018 ◽  
Vol 38 (9) ◽  
pp. 2185
Author(s):  
Xiaojun Li ◽  
Wanbin Zhang ◽  
Shuanhu Gao
Keyword(s):  
Natural Products ◽  
Chemical Synthesis ◽  
Total Synthesis

Nitropyrrole natural products: isolation, biosynthesis and total synthesis

2016 ◽  
Vol 14 (24) ◽  
pp. 5390-5401 ◽  
Author(s):  
Xiao-Bo Ding ◽  
Margaret A. Brimble ◽  
Daniel P. Furkert
Keyword(s):  
Natural Products ◽  
Biological Activity ◽  
Chemical Synthesis ◽  
Total Synthesis

A review of the isolation, biological activity, biosynthesis and chemical synthesis of nitropyrrole-containing natural products reported to date, including the pyrrolomycins, heronapyrroles and nitropyrrolins.

Enantioselective Syntheses of Yohimbine Alkaloids: Proving Grounds for New Catalytic Transformations

Synthesis ◽  
2021 ◽  
Author(s):  
Karl A. Scheidt ◽  
Eric R Miller
Keyword(s):  
Natural Products ◽  
Chemical Synthesis ◽  
Total Synthesis ◽  
State Of The Art ◽  
The State ◽  
Catalytic Transformations ◽  
Bond Forming ◽  
The Past ◽  
Catalytic Asymmetric ◽  
Enantioselective Syntheses

The total synthesis of bioactive alkaloids is an enduring challenge and an indication of the state of the art of chemical synthesis. With the explosion of catalytic asymmetric methods over the past three decades, these compelling targets have been fertile proving grounds for enantioselective bond forming transformations. We summarize these activities herein both to highlight the power and versatility of these methods and to instill future inspiration for new syntheses of these privileged natural products.

scholarly journals Unified Total Synthesis of the Brevianamide Alkaloids Enabled by Chemical Investigations into their Biosynthesis.

2021 ◽  
Author(s):  
Robert C. Godfrey ◽  
Helen E. Jones ◽  
Nicholas J. Green ◽  
Andrew L. Lawrence
Keyword(s):  
Natural Products ◽  
Chemical Synthesis ◽  
Total Synthesis ◽  
Scientific Community ◽  
Biological Activities ◽  
Focus Of Attention ◽  
Complex Structures ◽  
Biosynthetic Pathways ◽  
Synthetic Strategy ◽  
Synthetic Studies

The bicyclo[2.2.2]diazaoctane alkaloids are a vast group of natural products which have been the focus of attention from the scientific community for several decades. This interest stems from their broad range of biological activities, their diverse biosynthetic origins, and their topologically complex structures, which combined make them enticing targets for chemical synthesis. In this article, full details of our synthetic studies into the chemical feasibility of a proposed network of biosynthetic pathways towards the brevianamide family of bicyclo[2.2.2]diazaoctane alkaloids are disclosed. Insights into issues of reactivity and selectivity in the biosynthesis of these structures have aided the development of a unified biomimetic synthetic strategy, which has resulted in the total synthesis of all known bicyclo[2.2.2]diazaoctane brevianamides and the anticipation of an as-yet-undiscovered congener.

Computationally Augmented Retrosynthesis: Total Synthesis of Paspaline A and Emindole PB

2018 ◽  
Author(s):  
Timothy Newhouse ◽  
Daria E. Kim ◽  
Joshua E. Zweig
Keyword(s):  
Chemical Synthesis ◽  
Total Synthesis ◽  
Small Molecules ◽  
First Principles ◽  
Quantum Chemical ◽  
Computational Analysis ◽  
Empirical Evaluation ◽  
Synthetic Strategy ◽  
Catalyzed Reactions ◽  
Enzyme Catalyzed Reactions

The diverse molecular architectures of terpene natural products are assembled by exquisite enzyme-catalyzed reactions. Successful recapitulation of these transformations using chemical synthesis is hard to predict from first principles and therefore challenging to execute. A means of evaluating the feasibility of such chemical reactions would greatly enable the development of concise syntheses of complex small molecules. Herein, we report the computational analysis of the energetic favorability of a key bio-inspired transformation, which we use to inform our synthetic strategy. This approach was applied to synthesize two constituents of the historically challenging indole diterpenoid class, resulting in a concise route to (–)-paspaline A in 9 steps from commercially available materials and the first pathway to and structural confirmation of emindole PB in 13 steps. This work highlights how traditional retrosynthetic design can be augmented with quantum chemical calculations to reveal energetically feasible synthetic disconnections, minimizing time-consuming and expensive empirical evaluation.

Application of Dess-Martin oxidation in total synthesis of natural products

2020 ◽  
Vol 17 ◽  
Author(s):  
Majid M. Heravi ◽  
Tayebe Momeni ◽  
Vahideh Zadsirjan ◽  
Leila Mohammadi
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Selective Oxidation ◽  
Secondary Alcohols ◽  
Aldehydes And Ketones

: Dess–Martin periodinane (DMP), is a commercially available chemical, frequently being utilized as a mild oxidative agent for the selective oxidation of primary and secondary alcohols to their corresponding aldehydes and ketones, respectively. DMP shows several merits over other common oxidative agent such as chromium- and DMSO-based oxidants, thus it is habitually employed in the total synthesis of natural products. In this review, we try to underscore the applications of DMP as an effective oxidant in an appropriate step (steps) in the multistep total synthesis of natural products.

scholarly journals Non-Enzymatic Desymmetrization Reactions in Aqueous Media

Symmetry ◽  
2021 ◽  
Vol 13 (4) ◽  
pp. 720
Author(s):  
Satomi Niwayama
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Functional Groups ◽  
Organic Compounds ◽  
Recent Progress ◽  
Aqueous Media ◽  
Building Blocks ◽  
Organic Reactions ◽  
Environmentally Benign ◽  
Enzymatic Desymmetrization

Symmetric organic compounds are generally obtained inexpensively, and therefore they can be attractive building blocks for the total synthesis of various pharmaceuticals and natural products. The drawback is that discriminating the identical functional groups in the symmetric compounds is difficult. Water is the most environmentally benign and inexpensive solvent. However, successful organic reactions in water are rather limited due to the hydrophobicity of organic compounds in general. Therefore, desymmetrization reactions in aqueous media are expected to offer versatile strategies for the synthesis of a variety of significant organic compounds. This review focuses on the recent progress of desymmetrization reactions of symmetric organic compounds in aqueous media without utilizing enzymes.

Total synthesis: the structural confirmation of natural products

2021 ◽  
Vol 57 (27) ◽  
pp. 3307-3322
Author(s):  
Debobrata Paul ◽  
Ashis Kundu ◽  
Sanu Saha ◽  
Rajib Kumar Goswami
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Feature Article

This feature article highlights total synthesis as one of the reliable tools for the structural confirmation of natural products.

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