scholarly journals Recent Advances in the Total Synthesis of Tetramic Acid-Containing Natural Products

2016 ◽  
Vol 2016 ◽  
pp. 1-13 ◽  
Author(s):  
Wen-Ju Bai ◽  
Chen Lu ◽  
Xiqing Wang
Keyword(s):  
Organic Chemistry ◽  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Side Chain ◽  
Tetramic Acid ◽  
Unique Type ◽  
Recent Advances ◽  
Chemistry Community

With incredible bioactivities and fascinating structural complexities, tetramic acid- (TA-) containing natural products have attracted favorable attention among the organic chemistry community. Although the construction of the TA core is usually straightforward, the intricate C3-side chain sometimes asks for some deliberative strategy so as to fulfill an elegant total synthesis. This review mainly covers some exceptional synthetic examples for each type of natural product in recent years, showcasing the great achievements as well as unsettled obstacles in this area, in the hope of accelerating the synthetic and biological investigations for this unique type of natural product.

Recent advances in the synthesis of oxaspirolactones and their application in the total synthesis of related natural products

2019 ◽  
Vol 17 (31) ◽  
pp. 7270-7292 ◽  
Author(s):  
Sagar S. Thorat ◽  
Ravindar Kontham
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Medicinal Chemistry ◽  
Natural Product Chemistry ◽  
Structural Motifs ◽  
Recent Advances ◽  
Synthetic Molecules ◽  
Product Chemistry

Oxaspirolactones are ubiquitous structural motifs found in natural products and synthetic molecules with a diverse biochemical and physicochemical profile, and represent a valuable target in natural product chemistry and medicinal chemistry.

scholarly journals Recent advances in the total synthesis of cyclobutane-containing natural products

2020 ◽  
Vol 7 (1) ◽  
pp. 136-154 ◽  
Author(s):  
Jinshan Li ◽  
Kai Gao ◽  
Ming Bian ◽  
Hanfeng Ding
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Recent Advances ◽  
Recent Developments

Recent developments of strategies on the construction of cyclobutanes and their application in complex natural product synthesis are discussed.

Recent Advances on the Application of Electrocyclic Reactions in Complex Natural Product Synthesis

Synthesis ◽  
2017 ◽  
Vol 28 (19) ◽  
pp. 4383-4413 ◽  
Author(s):  
Ming Bian ◽  
Hanfeng Ding ◽  
Lekai Li
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Electrocyclic Reactions ◽  
Recent Advances ◽  
Electrocyclic Reaction

The electrocyclic reaction is one of the most powerful tools for the construction of complex polycyclic scaffolds in a highly stereocontrolled fashion. In this review, recent advances in its application in the total synthesis of representative natural products are discussed, with the aim of providing a complement to existing reviews.1 Introduction2 4π Electrocyclization2.1 Neutral 4π Electrocyclization2.2 Cationic 4π Electrocyclization3 6π Electrocyclization3.1 All-Carbon 6π Electrocyclization3.2 Oxa-6π Electrocyclization3.3 Aza-6π Electrocyclization3.4 Retro-6π Electrocyclization4 8π Electrocyclization5 Conclusion and Outlook

scholarly journals Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery

2014 ◽  
Vol 10 ◽  
pp. 1228-1232 ◽  
Author(s):  
Jens Schmidt ◽  
Zeinab Khalil ◽  
Robert J Capon ◽  
Christian B W Stark
Keyword(s):  
Antibacterial Activity ◽  
Natural Products ◽  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Natural Product ◽  
Joint Effort ◽  
Natural Product Biosynthesis ◽  
New Members ◽  
Degree Of Oxidation ◽  
Rare Class

The heronapyrroles A–C have first been isolated from a marine-derived Streptomyces sp. (CMB-0423) in 2010. Structurally, these natural products feature an unusual nitropyrrole system to which a partially oxidized farnesyl chain is attached. The varying degree of oxidation of the sesquiterpenyl subunit in heronapyrroles A–C provoked the hypothesis that there might exist other hitherto unidentified metabolites. On biosynthetic grounds a mono-tetrahydrofuran-diol named heronapyrrole D appeared a possible candidate. We here describe a short asymmetric synthesis of heronapyrrole D, its detection in cultivations of CMB-0423 and finally the evaluation of its antibacterial activity. We thus demonstrate that biosynthetic considerations and the joint effort of synthetic and natural product chemists can result in the identification of new members of a rare class of natural products.

scholarly journals Total Synthesis of the Reported Structure of Cahuitamycin A

2020 ◽  
Author(s):  
Justin Shapiro ◽  
Savannah Post ◽  
William Wuest
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Twelve Step ◽  
Target Compound ◽  
New Family ◽  
Iron Trafficking ◽  
Linear Sequence ◽  
Alternative Structure ◽  
Synthetic Target

In a 2016 screen of natural product extracts a new family of natural products, the cahuitamycins, was discovered and found to inhibit the formation of biofilms in the human pathogen <i>Acinetobacter baumannii</i>. The molecules contain an unusual piperazate residue that raises structure/function and biosynthesis questions and resemble iron-trafficking virulence factors from <i>A. baumannii</i>, suggesting a connection between metal homeostasis and biofilm-mediated pathogenicity. Here we disclose the first total synthesis of the reported structure of cahuitamycin A in a twelve-step longest linear sequence and 18% overall yield. Comparison of spectral data of the authentic natural product and synthetic target compound demonstrate that the reported structure is distinct from the isolated metabolite. Herein, we propose an alternative structure to reconcile our findings with the isolation report, setting the stage for future synthetic and biochemical investigations of an important class of natural products.

Recent advances in the intramolecular Mannich reaction in natural products total synthesis

2018 ◽  
Vol 5 (6) ◽  
pp. 1049-1066 ◽  
Author(s):  
Yingbo Shi ◽  
Qiaoling Wang ◽  
Shuanhu Gao
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Mannich Reaction ◽  
Recent Advances

This review focuses on selected applications of the intramolecular Mannich reaction as a key step in the total synthesis of natural products (2000–2017).

scholarly journals Synthetic study of ravidomycin, a hybrid natural product

2000 ◽  
Vol 72 (9) ◽  
pp. 1783-1786 ◽  
Author(s):  
Keisuke Suzuki
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Amino Sugar ◽  
Antitumor Antibiotics ◽  
Ready Availability ◽  
Silyl Acetals ◽  
Gilvocarcin V ◽  
Absolute Stereochemistry

Strategies and tactics associated with the total synthesis of hybrid natural products are discussed. The target is ravidomycin (2), one of the gilvocarcin-class antitumor antibiotics with an aryl C-glycoside structure. The first total synthesis of 2, which was achieved along similar lines of that of gilvocarcin V (1), served for the determination of the relative as well as the absolute stereochemistry of 2. Also revealed was a limitation of the synthetic scheme so long as the amino sugar congener was concerned. A preliminary result is discussed on the [2+2+2] approach that relies on the ready availability of various benzocyclobutene derivatives via regioselective [2+2] cycloaddition of α-alkoxybenzynes and ketene silyl acetals.

scholarly journals Harnessing the biocatalytic potential of iron- and α-ketoglutarate-dependent dioxygenases in natural product total synthesis

2020 ◽  
Vol 37 (8) ◽  
pp. 1065-1079 ◽  
Author(s):  
Christian R. Zwick ◽  
Hans Renata
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Oxidative Transformations

This review highlights recent chemoenzymatic syntheses of natural products that feature strategic applications of oxidative transformations with Fe/αKG enzymes.

Synthesis of Dichotomin A: Use of a Penicillamine-Derived Pseudoproline to Furnish Native Valine Residues

2015 ◽  
Vol 68 (4) ◽  
pp. 627 ◽  
Author(s):  
Michelle S. Y. Wong ◽  
Deni Taleski ◽  
Katrina A. Jolliffe
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Side Chain ◽  
Linear Peptide ◽  
Cyclic Hexapeptide ◽  
Peptide Precursors ◽  
Head To Tail Cyclization

The total synthesis of cyclic hexapeptide dichotomin A from linear peptide precursors containing penicillamine-derived pseudoproline residues is reported. The incorporation of a pseudoproline residue led to a faster reaction and higher head-to-tail cyclization yields in comparison to linear precursors containing the native valine residue. However, deprotection of the pseudoproline resulted in significant amounts of a by-product in which a threonine side chain had undergone dehydration, resulting in a low overall yield of the natural product.

scholarly journals The quest for supernatural products: the impact of total synthesis in complex natural products medicinal chemistry

2020 ◽  
Vol 37 (11) ◽  
pp. 1511-1531
Author(s):  
Zhi-Chen Wu ◽  
Dale L. Boger
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Medicinal Chemistry ◽  
Recent Advances ◽  
The Impact

This review summarizes and highlights recent advances in medicinal chemistry of natural products enabled by total synthesis that provide “supernatural products” with improved properties superseding the natural products themselves.

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