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Stereoselective total syntheses of (±)-arthrinone and related natural compounds

✍ Scribed by Masahiko Uchiyama; Yoshiyuki Kimura; Akihiro Ohta

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
79 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

The first total syntheses of (±)-arthrinone, (±)-1-dehydroxyarthrinone, and (±)-3a,9a-deoxy-3a-hydroxy-1-dehydroxyarthrinone, antifungal metabolites from the coprophilous fungus Cercophora sordarioides, were accomplished in a stereoselective manner. The ring systems of these metabolites, which were rare among natural products, were efficiently and diastereoselectively assembled using the [2,3]Wittig rearrangement and Diels-Alder reaction as the key steps.

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