JOURNAL ARTICLE

Nature-Inspired Total\nSynthesis of (−)-Fusarisetin\nA

Abstract

A concise, protecting group-free total synthesis of (−)-fusarisetin\nA (<b>1</b>) was efficiently achieved in nine steps from commercially\navailable (<i>S</i>)-(−)-citronellal. The synthetic\napproach was inspired by our proposed biosynthesis of <b>1</b>. Key transformations of our strategy include a facile construction\nof the decalin moiety that is produced via a stereoselective IMDA\nreaction and a one-pot TEMPO-induced radical cyclization/aminolysis\nthat forms the C ring of <b>1</b>. Our route is amenable to\nanalogue synthesis for biological evaluation.

Keywords:
Moiety Stereoselectivity Ring (chemistry) Total synthesis Depsipeptide

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Topics

Flavonoids in Medical Research
Health Sciences →  Medicine →  Pharmacology
Bioactive Natural Diterpenoids Research
Life Sciences →  Biochemistry, Genetics and Molecular Biology →  Molecular Biology
Fungal Biology and Applications
Health Sciences →  Medicine →  Pharmacology

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