scholarly journals Construction of a diverse set of terpenoid decalin subunits from a common enantiomerically pure scaffold obtained by a biomimetic cationic cyclization

2018 ◽  
Vol 54 (78) ◽  
pp. 11025-11028 ◽  
Author(s):  
Raquel Fontaneda ◽  
Francisco J. Fañanás ◽  
Félix Rodríguez
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Potential Application ◽  
Cyclization Reaction ◽  
Enantiomerically Pure ◽  
Cationic Cyclization

An unprecedented biomimetic cationic cyclization reaction is used for the synthesis of an enantiomerically pure scaffold that is easily transformed into a set of structurally diverse decalin derivatives with potential application in the synthesis of targeted natural products and/or natural-product-inspired new molecules.

Other Methods for C–C Ring Construction: Pinolinone (Bach), Agelastatin A (Batey), Panaginsene (Lee), Salvileucalin D, Salvileucalin C (Ding), ent-Codeine (Hudlicky), Walsucochin B (Xie/Shi)

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Natural Product ◽  
Conjugate Addition ◽  
Chiral Medium ◽  
Relative Configuration ◽  
Enantiomerically Pure ◽  
Methyl Group ◽  
University Of Toronto ◽  
Agelastatin A ◽  
Cationic Cyclization ◽  
The University

Thorsten Bach of the Technische Universität München used (Chem. Commun. 2014, 50, 3353) the chiral medium-mediated photochemical 2+2 cycloaddition that he devel­oped to prepare 3 by combining 1 with 2. Oxidative cleavage led to (−)-pinolinone 4. Robert A. Batey of the University of Toronto rearranged (Angew. Chem. Int. Ed. 2013, 52, 10862) furfural 5 in the presence of 6 to give the enone 7. Acylation fol­lowed by intramolecular conjugate addition delivered agelastatin A 8. Hee-Yoon Lee of KAIST prepared (Org. Lett. 2014, 16, 2466) the tosylhydrazone Na salt 9 from citronellal. Thermolysis led, via a dialkyl diazo intermediate, to the tricy­clic 10. Direct comparison of synthetic material with the natural product panaginsene 11 enabled the assignment of the relative configuration of the pendant methyl group. Hanfeng Ding of Zhejiang University eliminated (Org. Lett. 2014, 16, 3376) HBr from 12 to give, after rearrangement, the cycloheptadiene salvileucalin D 13. Irradiation converted 13 to the cyclobutene salvileucalin C 14. In a recent chapter of his continuing work on the morphine alkaloids, Tomas Hudlicky of Brock University described (Adv. Synth. Catal. 2014, 356, 333) the intra­molecular [3+2] cycloaddition of the nitrone derived from 15 to give 16. This was readily carried on to ent-codeine 17. Xingang Xie and Xuegong She of Lanzhou University used (Org. Lett. 2014, 16, 1996) Shi epoxidation and Itsuno–Corey reduction to prepare 18 in enantiomerically-pure form. Cationic cyclization converted 18 to 19, that was oxidized to (−)-walsucochin B 20.

Synthesis and Biological Evaluation of the Antimicrobial Natural Product Lipoxazolidinone A

2018 ◽  
Author(s):  
Jonathan J. Mills ◽  
Kaylib R. Robinson ◽  
Troy E. Zehnder ◽  
Joshua G. Pierce
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Mechanism Of Action ◽  
Marine Natural Products ◽  
Biological Evaluation ◽  
Lead Compounds ◽  
Follow Up Studies ◽  
Initial Resistance ◽  
Synthesis And Biological Evaluation

The lipoxazolidinone family of marine natural products, with an unusual 4-oxazolidinone heterocycle at their core, represents a new scaffold for antimicrobial discovery; however, questions regarding their mechanism of action and high lipophilicity have likely slowed follow-up studies. Herein, we report the first synthesis of lipoxazolidinone A, 15 structural analogs to explore its active pharmacophore, and initial resistance and mechanism of action studies. These results suggest that 4-oxazolidinones are valuable scaffolds for antimicrobial development and reveal simplified lead compounds for further optimization.

Unzipping Natural Products: Improved Natural Product Structure Predictions by Ensemble Modeling and Fingerprint Matching

2018 ◽  
Author(s):  
William A. Shirley ◽  
Brian P. Kelley ◽  
Yohann Potier ◽  
John H. Koschwanez ◽  
Robert Bruccoleri ◽  
...  
Keyword(s):  
Natural Products ◽  
Open Source ◽  
Natural Product ◽  
Gene Cluster ◽  
Public Domain ◽  
Product Structure ◽  
Fingerprint Matching ◽  
Ensemble Modeling ◽  
Chemical Structures ◽  
Source Gene

This pre-print explores ensemble modeling of natural product targets to match chemical structures to precursors found in large open-source gene cluster repository antiSMASH. Commentary on method, effectiveness, and limitations are enclosed. All structures are public domain molecules and have been reviewed for release.

Recent Progress Towards Synthesis of the Indolizidine Alkaloid 195B

2020 ◽  
Vol 17 (2) ◽  
pp. 82-90 ◽  
Author(s):  
Ghodsi Mohammadi Ziarani ◽  
Fatemeh Mohajer ◽  
Zohreh kheilkordi
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Recent Progress ◽  
Human Life ◽  
Natural Compounds ◽  
Biologically Active ◽  
Pharmaceutical Chemistry ◽  
Biological Perspective ◽  
Highly Active

Background: Natural products have been received attention due to their importance in human life as those are biologically active. In this review, there are some reports through different methods related to the synthesis of the indolizidine 195B which was extracted from poisonous frog; however, due to respect nature, the synthesis of natural compounds such as indolizidine has been attracted much attention among scientists and researchers. Objective: This review discloses the procedures and methods to provide indolizidine 195B from 1989 to 2018 due to their importance as a natural product. Conclusion: There are several methods to give rise to the indolizidine 195B as a natural product that is highly active from the biological perspective in pharmaceutical chemistry. In summary, many protocols for the preparations of indolizidine 195B from various substrates, several reagents, and conditions have been reported from different aromatic and aliphatic.

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 Chemical Elicitors Induce Rare Bioactive Secondary Metabolites in Deep-Sea Bacteria under Laboratory Conditions

Metabolites ◽  
2021 ◽  
Vol 11 (2) ◽  
pp. 107
Author(s):  
Rafael de Felício ◽  
Patricia Ballone ◽  
Cristina Freitas Bazzano ◽  
Luiz F. G. Alves ◽  
Renata Sigrist ◽  
...  
Keyword(s):  
Natural Products ◽  
Secondary Metabolites ◽  
Natural Product ◽  
Deep Sea ◽  
Chemical Space ◽  
Bacterial Genome ◽  
Vast Number ◽  
Bacterial Metabolites ◽  
Laboratory Conditions ◽  
Deep Sea Bacteria

Bacterial genome sequencing has revealed a vast number of novel biosynthetic gene clusters (BGC) with potential to produce bioactive natural products. However, the biosynthesis of secondary metabolites by bacteria is often silenced under laboratory conditions, limiting the controlled expression of natural products. Here we describe an integrated methodology for the construction and screening of an elicited and pre-fractionated library of marine bacteria. In this pilot study, chemical elicitors were evaluated to mimic the natural environment and to induce the expression of cryptic BGCs in deep-sea bacteria. By integrating high-resolution untargeted metabolomics with cheminformatics analyses, it was possible to visualize, mine, identify and map the chemical and biological space of the elicited bacterial metabolites. The results show that elicited bacterial metabolites correspond to ~45% of the compounds produced under laboratory conditions. In addition, the elicited chemical space is novel (~70% of the elicited compounds) or concentrated in the chemical space of drugs. Fractionation of the crude extracts further evidenced minor compounds (~90% of the collection) and the detection of biological activity. This pilot work pinpoints strategies for constructing and evaluating chemically diverse bacterial natural product libraries towards the identification of novel bacterial metabolites in natural product-based drug discovery pipelines.

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

scholarly journals MeFSAT: a curated natural product database specific to secondary metabolites of medicinal fungi

RSC Advances ◽  
2021 ◽  
Vol 11 (5) ◽  
pp. 2596-2607
Author(s):  
R. P. Vivek-Ananth ◽  
Ajaya Kumar Sahoo ◽  
Kavyaa Kumaravel ◽  
Karthikeyan Mohanraj ◽  
Areejit Samal
Keyword(s):  
Natural Products ◽  
Secondary Metabolites ◽  
Natural Product ◽  
Chemical Space ◽  
Therapeutic Uses ◽  
Medicinal Fungi ◽  
Fungal Natural Products

First dedicated manually curated resource on secondary metabolites and therapeutic uses of medicinal fungi. Cheminformatics based analysis of the chemical space of fungal natural products.

scholarly journals Natural product fragment combination to performance-diverse pseudo-natural products

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Michael Grigalunas ◽  
Annina Burhop ◽  
Sarah Zinken ◽  
Axel Pahl ◽  
José-Manuel Gally ◽  
...  
Keyword(s):  
Natural Products ◽  
Product Design ◽  
Natural Product ◽  
Chemical Space ◽  
Biological Evaluation ◽  
Product Structure ◽  
Biologically Relevant ◽  
Biologically Relevant Chemical Space

AbstractNatural product structure and fragment-based compound development inspire pseudo-natural product design through different combinations of a given natural product fragment set to compound classes expected to be chemically and biologically diverse. We describe the synthetic combination of the fragment-sized natural products quinine, quinidine, sinomenine, and griseofulvin with chromanone or indole-containing fragments to provide a 244-member pseudo-natural product collection. Cheminformatic analyses reveal that the resulting eight pseudo-natural product classes are chemically diverse and share both drug- and natural product-like properties. Unbiased biological evaluation by cell painting demonstrates that bioactivity of pseudo-natural products, guiding natural products, and fragments differ and that combination of different fragments dominates establishment of unique bioactivity. Identification of phenotypic fragment dominance enables design of compound classes with correctly predicted bioactivity. The results demonstrate that fusion of natural product fragments in different combinations and arrangements can provide chemically and biologically diverse pseudo-natural product classes for wider exploration of biologically relevant chemical space.

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