Synthesis of the octahydronaphthalene core of nahuoic acid A via a B(C 6 F 5 ) 3 -catalyzed intramolecular Diels-Alder (IMDA) reaction

Model tetraenal 9b underwent intramolecular Diels-Alder cycloaddition in CH Cl at -10 °C under catalysis by the bulky Lewis acid B(C F ) to deliver as major components the cis-fused angularly-methylated octahydronaphthalene products, which are formed through the alternative exo orientations of the r...

Full description

Saved in:
Bibliographic Details
Published in:Organic & biomolecular chemistry 2017-09, Vol.15 (35), p.7430-7438
Main Authors: Guillade, Lucía, González-Pérez, Adán B, de Lera, Ángel R
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Model tetraenal 9b underwent intramolecular Diels-Alder cycloaddition in CH Cl at -10 °C under catalysis by the bulky Lewis acid B(C F ) to deliver as major components the cis-fused angularly-methylated octahydronaphthalene products, which are formed through the alternative exo orientations of the reacting moieties. One of these diastereomers features the relative and absolute configuration present in the core of nahuoic acid A, a natural product that acts as a cofactor-competitive inhibitor of the lysine methyl transferase SETD8. By contrast, catalysis of the reaction by Me AlCl at -40 °C selectively afforded the trans-fused isomer resulting from the Re-endo orientation.
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob01665d