Combining biocatalysis and organocatalysis for the synthesis of piperidine alkaloids.

2022 ◽  
Author(s):  
Freya Taday ◽  
Ryan Cairns ◽  
Adam O'Connell ◽  
Elaine O'Reilly
Keyword(s):  
Natural Products ◽  
Building Blocks ◽  
Piperidine Alkaloids ◽  
Bioactive Natural Products ◽  
Cascade Processes

There is continued interest in developing cascade processes for the synthesis of key chiral building blocks and bioactive natural products (or analogues). Here, we report a hybrid bio-organocatalytic cascade for...

Formation of Carbon-Oxygen Bond Mediated by Hypervalent Iodine Reagents Under Metal-free Conditions

2020 ◽  
Vol 17 ◽  
Author(s):  
Ayesha Jalil ◽  
Yaxin O Yang ◽  
Zhendong Chen ◽  
Rongxuan Jia ◽  
Tianhao Bi ◽  
...  
Keyword(s):  
Natural Products ◽  
Bond Formation ◽  
Building Blocks ◽  
Review Article ◽  
Hypervalent Iodine ◽  
Metal Free ◽  
Bioactive Natural Products ◽  
The Past ◽  
Oxygen Bond ◽  
Privileged Scaffolds

: Hypervalent iodine reagents are a class of non-metallic oxidants have been widely used in the construction of several sorts of bond formations. This surging interest in hypervalent iodine reagents is essentially due to their very useful oxidizing properties, combined with their benign environmental character and commercial availability from the past few decades ago. Furthermore, these hypervalent iodine reagents have been used in the construction of many significant building blocks and privileged scaffolds of bioactive natural products. The purpose of writing this review article is to explore all the transformations in which carbon-oxygen bond formation occurred by using hypervalent iodine reagents under metal-free conditions

Electrocatalytic Difunctionalization of Olefins as a General Approach to the Synthesis of Vicinal Diamines

Synlett ◽  
2018 ◽  
Vol 29 (03) ◽  
pp. 257-265 ◽  
Author(s):  
Song Lin ◽  
Joseph Parry ◽  
Niankai Fu
Keyword(s):  
Natural Products ◽  
Building Blocks ◽  
Therapeutic Agents ◽  
Recent Contribution ◽  
Structural Motifs ◽  
Bioactive Natural Products ◽  
Methodological Approaches ◽  
Molecular Catalysts ◽  
Vicinal Diamines

Vicinal diamines are highly prevalent structural motifs in therapeutic agents, bioactive natural products, and molecular catalysts. However, there are currently few unified methodological approaches for making these pertinent synthetic building blocks. This Synpacts article provides an overview of selected landmark developments in the area of olefin diamination. In particular, we highlight our recent contribution on the electrocatalytic diazidation of olefins as a general, selective, and sustainable method for the synthesis of vicinal diamines.1 Introduction2 Background: Intermolecular Diamination of Olefins3 Background: Intermolecular Diazidation of Olefins4 Electrocatalytic Diazidation of Olefins

Recent developments in the synthesis of azaindoles from pyridine and pyrrole building blocks

2021 ◽  
Author(s):  
Damoder Reddy Motati ◽  
Radhika Amaradhi ◽  
Thota Ganesh
Keyword(s):  
Natural Products ◽  
Building Blocks ◽  
Bioactive Natural Products ◽  
Biological Importance ◽  
Recent Developments ◽  
Synthetic Approaches

The azaindole framework is ubiquitous in bioactive natural products and pharmaceuticals. This review highlights the synthetic approaches to azaindoles with advantages and limitations, mechanistic pathways and biological importance.

Sharpless Asymmetric Epoxidation: Applications in the Synthesis of Bioactive Natural Products

2020 ◽  
Vol 17 ◽  
Author(s):  
Suélen Karine Sartori ◽  
Izabel Luzia Miranda ◽  
Marisa Alves Nogueira Diaz ◽  
Gaspar Diaz-Muñoz
Keyword(s):  
Natural Products ◽  
Building Blocks ◽  
Heterocyclic Ring ◽  
Biologically Active ◽  
Asymmetric Epoxidation ◽  
Allylic Alcohols ◽  
Titanium Tetraisopropoxide ◽  
Bioactive Natural Products ◽  
Tert Butyl Hydroperoxide ◽  
Sharpless Asymmetric Epoxidation

: This review discusses an important synthetic tool proposed by K. B. Sharpless in 1980, known as the Sharpless asymmetric epoxidation of allylic alcohols, and examines its use in the total synthesis of representative exponents of biologically active natural products. Focus is given to the synthesis of simple to highly complex secondary metabolites, including lactones, amino acids, diterpenes, and macrolides. The Sharpless approach involves the use of a catalyst, titanium tetraisopropoxide [Ti(OiPr)4], dialkyl tartrate as chiral ligand, and tert-butyl hydroperoxide (TBHP) as oxidizing agent. The method allows converting allylic alcohols to epoxides, which are chiral building blocks and versatile intermediates in the synthesis of natural products. The biological and synthetic importance of epoxides lies in the susceptibility of the threemembered heterocyclic ring to stereo- and regioselective opening by nucleophilic or acidic reagents, providing oxygen adducts.

Hypervalent Iodine-Mediated Synthesis of Spiroheterocycles via Oxidative Cyclization

2019 ◽  
Vol 23 (1) ◽  
pp. 14-37 ◽  
Author(s):  
Linlin Xing ◽  
Yong Zhang ◽  
Yunfei Du
Keyword(s):  
Natural Products ◽  
Building Blocks ◽  
Review Article ◽  
Oxidative Cyclization ◽  
Hypervalent Iodine ◽  
Metal Free ◽  
Bioactive Natural Products ◽  
Privileged Scaffolds

Hypervalent iodine reagents have been widely used in the construction of many important building blocks and privileged scaffolds of bioactive natural products. This review article aims to briefly discuss strategies that have used hypervalent iodine reagents as oxidants to synthesize spiroheterocyclic compounds and to stimulate further study for novel syntheses of spiroheterocyclic core structures using hypervalent iodine reagents under metal-free conditions.

Progress in the synthesis of N-acyl-N,O-acetals

Synthesis ◽  
2021 ◽  
Author(s):  
Xiao-Yan Ma ◽  
Fu-Qiang Shao ◽  
Xinjun Hu ◽  
Xingyong Liu
Keyword(s):  
Natural Products ◽  
Electrochemical Oxidation ◽  
Organic Synthesis ◽  
Building Blocks ◽  
Synthetic Methods ◽  
Chemical Methods ◽  
Bioactive Natural Products

N-Acyl-N,O-acetals are key component a variety of bioactive natural products. Furthermore， they are synthetic equivalents of unstable N-acylimines and building blocks in organic synthesis. Tremendous efforts have been made to the synthesis of such acetals, these methods can roughly be classified into two categories: electrochemical oxidation and chemical methods. Herein, we want to summarize the progress made on the preparation of the subunits, which may provide assistance for the development of new synthetic methods of N-acyl-N,O-acetals.

scholarly journals Amino acid motifs in natural products: synthesis of O-acylated derivatives of (2S,3S)-3-hydroxyleucine

2014 ◽  
Vol 10 ◽  
pp. 1135-1142 ◽  
Author(s):  
Oliver Ries ◽  
Martin Büschleb ◽  
Markus Granitzka ◽  
Dietmar Stalke ◽  
Christian Ducho
Keyword(s):  
Natural Products ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Building Blocks ◽  
Synthetic Approach ◽  
Protecting Group ◽  
Nucleoside Antibiotics ◽  
Bioactive Natural Products ◽  
Sar Studies ◽  
Derivatives Of

(2S,3S)-3-Hydroxyleucine can be found in an increasing number of bioactive natural products. Within the context of our work regarding the total synthesis of muraymycin nucleoside antibiotics, we have developed a synthetic approach towards (2S,3S)-3-hydroxyleucine building blocks. Application of different protecting group patterns led to building blocks suitable for C- or N-terminal derivatization as well as for solid-phase peptide synthesis. With respect to according motifs occurring in natural products, we have converted these building blocks into 3-O-acylated structures. Utilizing an esterification and cross-metathesis protocol, (2S,3S)-3-hydroxyleucine derivatives were synthesized, thus opening up an excellent approach for the synthesis of bioactive natural products and derivatives thereof for structure activity relationship (SAR) studies.

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