Unified Total Synthesis of Diverse Meroterpenoids from Ganoderma Applanatum

A unified approach to meroterpenoids applanatumols B, V, W, X, and Y produced by the medicinal fungus Ganoderma applanatum and 2′-epi-spiroapplanatumine O is presented. The key synthetic sequence consists of a tandem anionic ketone allylation/oxy-Cope rearrangement/α-oxygenation furnishing an α-amin...

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Published inOrganic letters Vol. 24; no. 25; pp. 4552 - 4556
Main Authors Šimek, Michal, Bártová, Kateřina, Issad, Samy, Hájek, Miroslav, Císařová, Ivana, Jahn, Ullrich
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.07.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MILD
DEBENZYLATION
ALDEHYDES
EFFICIENT
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Summary:A unified approach to meroterpenoids applanatumols B, V, W, X, and Y produced by the medicinal fungus Ganoderma applanatum and 2′-epi-spiroapplanatumine O is presented. The key synthetic sequence consists of a tandem anionic ketone allylation/oxy-Cope rearrangement/α-oxygenation furnishing an α-aminoxy ketone and a persistent radical effect-based 5-exo-trig cyclization leading to the trisubstituted cyclopentane core. The relative configuration of applanatumol V has to be revised. Some compounds display significant cytotoxic and antioxidant properties.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01633