Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 20, Issue 46, Pages 9138-9141Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2ob01839j
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- JSPS KAKENHI [JP21K14797, JP19K06981]
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In this study, total syntheses of four Ganoderma-derived meroterpenoids were reported. A flexible approach was developed to construct the 3-alkyl-5-aryl-gamma-butenolide skeleton, a common motif of these meroterpenoids. The target compounds were synthesized with enantioselective access and moderate overall yields.
In this study, we report the total syntheses of Ganoderma-derived meroterpenoids, (-)-oregonensin A, (-)-chizhine E, (-)-applanatumol U, and (-)-ent-fornicin A. The 3-alkyl-5-aryl-gamma-butenolide skeleton, a common motif of these meroterpenoids, was constructed through the enantioselective reductive lactonization of the gamma-keto ester, alkylation, and sulfoxide-beta-syn-elimination. This flexible approach enabled enantioselective access to these meroterpenoids with the longest linear sequence of 6-8 steps, and in 21-36% overall yield, respectively.
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