Synthesis of the octahydronaphthalene core of nahuoic acid A: Via a B(CF)-catalyzed intramolecular Diels-Alder (IMDA) reaction
Organic and Biomolecular Chemistry, ISSN: 1477-0520, Vol: 15, Issue: 35, Page: 7430-7438
2017
- 4Citations
- 9Captures
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Example: if you select the 1-year option for an article published in 2019 and a metric category shows 90%, that means that the article or review is performing better than 90% of the other articles/reviews published in that journal in 2019. If you select the 3-year option for the same article published in 2019 and the metric category shows 90%, that means that the article or review is performing better than 90% of the other articles/reviews published in that journal in 2019, 2018 and 2017.
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Metrics Details
- Citations4
- Citation Indexes4
- CrossRef3
- Captures9
- Readers9
Article Description
Model tetraenal 9b underwent intramolecular Diels-Alder cycloaddition in CHCl at -10 °C under catalysis by the bulky Lewis acid B(CF) 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 MeAlCl at -40 °C selectively afforded the trans-fused isomer resulting from the Re-endo orientation.
Bibliographic Details
http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=85029583802&origin=inward; http://dx.doi.org/10.1039/c7ob01665d; http://www.ncbi.nlm.nih.gov/pubmed/28831488; https://xlink.rsc.org/?DOI=C7OB01665D; http://xlink.rsc.org/?DOI=C7OB01665D; http://pubs.rsc.org/en/content/articlepdf/2017/OB/C7OB01665D; https://dx.doi.org/10.1039/c7ob01665d; https://pubs.rsc.org/en/content/articlelanding/2017/ob/c7ob01665d
Royal Society of Chemistry (RSC)
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