scholarly journals Multigram Scale Total Synthesis of Piperarborenines C-E

2021 ◽  
Author(s):  
Jason Lenihan ◽  
Matthew Mailloux ◽  
Aaron Beeler
Keyword(s):  
Total Synthesis ◽  
Biological Properties ◽  
Direct Excitation ◽  
Pentafluorophenyl Ester ◽  
Scalable Synthesis ◽  
Uv Leds ◽  
Cryogenic Conditions ◽  
Key Innovations

We report the development of a multigram scale total synthesis of heterodimeric β-truxinic imides piperarborenines C-E using a catechol-mediated diastereoselective intramolecular [2+2] photocycloaddition. Key innovations lie in the use of (1) catechol as a highly selective auxiliary for the robust and scalable synthesis of homo- and heterodimeric β-truxinates, (2) UV LEDs for direct excitation in the [2+2] cycloaddition step, and (3) a bis pentafluorophenyl ester and LDA for the challenging installation of the syn dihydropyridinone imides. This approach is exceptionally scalable – requiring minimal chromatography, no photocatalysts, and no cryogenic conditions - and will enable thorough evaluation of the biological properties and anticancer profiles of piperaborenines C-E and derivatives thereof.

The Total Synthesis and Biological Properties of the Cytotoxic Macrolide FD-891 (Ia) and Its Non-Natural (Z)-C12 Isomer (Ib).

ChemInform ◽  
2007 ◽  
Vol 38 (42) ◽  
Author(s):  
Jorge Garcia-Fortanet ◽  
Juan Murga ◽  
Miguel Carda ◽  
J. Alberto Marco ◽  
Ruth Matesanz ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Biological Properties ◽  
Cytotoxic Macrolide

Enantio- and Diastereoselective Total Synthesis of (+)-Panepophenanthrin, a Ubiquitin-Activating Enzyme Inhibitor, and Biological Properties of Its New Derivatives

2006 ◽  
Vol 1 (6) ◽  
pp. 845-851 ◽  
Author(s):  
Masayoshi Matsuzawa ◽  
Hideaki Kakeya ◽  
Junichiro Yamaguchi ◽  
Mitsuru Shoji ◽  
Rie Onose ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Enzyme Inhibitor ◽  
Biological Properties

Total Synthesis of DHA and DPAn-3 non-enzymatic oxylipins

Synthesis ◽  
2021 ◽  
Author(s):  
alexandre guy ◽  
Jérémy Merad ◽  
Thomas Degrange ◽  
Guillaume Reversat ◽  
Valérie Bultel-Poncé ◽  
...  
Keyword(s):  
Oxidative Stress ◽  
Fatty Acids ◽  
Docosahexaenoic Acid ◽  
Polyunsaturated Fatty Acids ◽  
Total Synthesis ◽  
Biological Properties ◽  
Chemical Structures ◽  
Structural Variety ◽  
Synthetic Strategy

Oxylipins are formed in-vivo from polyunsaturated fatty acids (PUFAs). A large structural variety of compounds is grouped under the term oxylipins, which differ from their formation mechanism (involving enzymes or not), as well as their chemical structures (cyclopentanes, tetrahydrofurans, hydroxylated-PUFA etc.). All structures of oxylipins are of great biological interests. Directly correlated to oxidative stress phenomenon, non-enzymatic oxylipins are used as systemic and/or specific biomarkers in various pathologies and more especially, they were found to have their own biological properties. Produced in-vivo as a non-separable mixture of isomers, total synthesis is a keystone to answer biological questions. In this work, we described the total synthesis of three non-enzymatic oxylipins derived from docosahexaenoic acid (DHA) and docosapentanoic acid (DPAn-3) using a unique and convergent synthetic strategy.

scholarly journals First Synthesis of (−)-Altenuene-D3 Suitable as Internal Standard for Isotope Dilution Mass Spectrometry

Molecules ◽  
2019 ◽  
Vol 24 (24) ◽  
pp. 4563
Author(s):  
Michael A. Sebald ◽  
Julian Gebauer ◽  
Thomas Sommerfeld ◽  
Matthias Koch
Keyword(s):  
Mass Spectrometry ◽  
Antimicrobial Activity ◽  
Stable Isotope ◽  
Total Synthesis ◽  
Isotope Dilution ◽  
Isotope Dilution Mass Spectrometry ◽  
Internal Standard ◽  
Biological Properties ◽  
Mycotoxin Analysis ◽  
Activity Optimization

Metabolites from Alternaria fungi exhibit a variety of biological properties such as phytotoxic, cytotoxic, or antimicrobial activity. Optimization of a literature procedure culminated in an efficient total synthesis of (−)-altenuene as well as a stable isotope-labeled derivative suitable for implementation in a LC-MS/MS method for mycotoxin analysis.

scholarly journals Total Synthesis of Caprazamycin A: Practical and Scalable Synthesis of syn-β-Hydroxyamino Acids and Introduction of a Fatty Acid Side Chain to 1,4-Diazepanone

2019 ◽  
Vol 141 (21) ◽  
pp. 8527-8540 ◽  
Author(s):  
Hugh Nakamura ◽  
Chihiro Tsukano ◽  
Takuma Yoshida ◽  
Motohiro Yasui ◽  
Shinsuke Yokouchi ◽  
...  
Keyword(s):  
Fatty Acid ◽  
Total Synthesis ◽  
Side Chain ◽  
Hydroxyamino Acids ◽  
Scalable Synthesis

Yatakemycin: total synthesis, DNA alkylation, and biological properties

2008 ◽  
Vol 25 (2) ◽  
pp. 220-226 ◽  
Author(s):  
Mark S. Tichenor ◽  
Dale L. Boger
Keyword(s):  
Total Synthesis ◽  
Biological Properties ◽  
Dna Alkylation

Enantio- and Diastereoselective Total Synthesis of (+)-Panepophenanthrin (I), a Ubiquitin-Activating Enzyme Inhibitor, and Biological Properties of Its New Derivatives.

ChemInform ◽  
2007 ◽  
Vol 38 (16) ◽  
Author(s):  
Masayoshi Matsuzawa ◽  
Hideaki Kakeya ◽  
Junichiro Yamaguchi ◽  
Mitsuru Shoji ◽  
Rie Onose ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Enzyme Inhibitor ◽  
Biological Properties

Scalable total synthesis of piceatannol-3'-O-β-D-glucopyranoside and the 4'-methoxy congener thereof: An early stage glycosylation strategy

Synthesis ◽  
2021 ◽  
Author(s):  
Jianfeng Li ◽  
Xiaoting Wang ◽  
Rongping Zhang ◽  
Lei Chen
Keyword(s):  
Total Synthesis ◽  
Heck Reaction ◽  
Early Stage ◽  
Phenolic Glycoside ◽  
Acidic Conditions ◽  
Scalable Synthesis ◽  
Glycosylation Reaction

Scalable synthesis of piceatannol-3'-O-β-D-glucopyranoside and the 4'-methoxy congener thereof were achieved. This route features an early implemented Fischer-like glycosylation reaction, a regioselective iodination of phenolic glycoside under strongly acidic conditions, a highly telescoped route to access the styrene derivative and a key Mizoroki-Heck reaction to render the desired coupled products in high overall yield.

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