Enantioselective total synthesis of (‒)-lucidumone enabled by tandem prins cyclization/cycloetherification sequence

Xian-Zhang Liao, Ran Wang, Xin Wang and Guang Li ()
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Xian-Zhang Liao: Chinese Academy of Medical Sciences & Peking Union Medical College
Ran Wang: Chinese Academy of Medical Sciences & Peking Union Medical College
Xin Wang: Chinese Academy of Medical Sciences & Peking Union Medical College
Guang Li: Chinese Academy of Medical Sciences & Peking Union Medical College

Nature Communications, 2024, vol. 15, issue 1, 1-7

Abstract: Abstract The Ganoderma meroterpenoids are a growing class of natural products with architectural complexity, and exhibit a wide range of biological activities. Here, we report an enantioselective total synthesis of the Ganoderma meroterpenoid (‒)-lucidumone. The synthetic route features several key transformations, including a) a Cu-catalyzed enantioselective silicon-tethered intramolecular Diels-Alder cycloaddition to construct the highly functionalized bicyclo[2.2.2]octane moiety; b) Brønsted acid promoted tandem O-deprotection/Prins cyclization/Cycloetherification sequence followed by oxidation to install concurrently the tetrahydrofuran and the fused indanone framework; c) Fleming-Tamao oxidation to generate the secondary hydroxyl; d) an iron-catalyzed Wacker-type oxidation of hindered vinyl group to methyl ketone.

Date: 2024
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DOI: 10.1038/s41467-024-46896-3

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