Total synthesis of nahuoic acid A via a putative biogenetic intramolecular Diels–Alder (IMDA) reaction-Reference-Cited by-同舟云学术

Total synthesis of nahuoic acid A via a putative biogenetic intramolecular Diels–Alder (IMDA) reaction

Published:2021 Issue:45 Volume:12 Page:15157-15169
ISSN:2041-6520
Container-title:Chemical Science
language:en
Short-container-title:Chem. Sci.

Author:

Guillade Lucía¹,Mora Paula¹,Villar Pedro¹^ORCID,Alvarez Rosana¹^ORCID,R. de Lera Angel¹^ORCID

Affiliation:

1. Departamento de Química Orgánica, Facultade de Química, CINBIO, IIS Galicia Sur, Universidade de Vigo, 36310 Vigo, Spain

Abstract

The total synthesis of natural product nahuoic acid A, a cofactor-competitive inhibitor of the epigenetic enzyme lysine methyl transferase SETD8, has been carried out based on the biogenetic proposal of an intramolecular Diels–Alder (IMDA) cycloaddition.

Funder

Ministerio de Economía y Competitividad

Xunta de Galicia

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2021/SC/D1SC04524E

Reference116 articles.

1. Nahuoic Acid A Produced by a Streptomyces sp. Isolated From a Marine Sediment Is a Selective SAM-Competitive Inhibitor of the Histone Methyltransferase SETD8

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3. Analysis of two carbon-13 NMR correlations for determining the stereochemistry of 1,3-diol acetonides

4. Nuclear magnetic resonance enantiomer regents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and .alpha.-methoxy-.alpha.-trifluoromethylphenylacetate (MTPA) esters

5. Mosher ester analysis for the determination of absolute configuration of stereogenic (chiral) carbinol carbons

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