Biomimetic Total Synthesis of Clavicipitic Acid: A DDQ-Mediated Intramolecular Cross-Dehydrogenative Coupling Approach

Clavicipitic acid, a communesin alkaloid precursor, has attracted significant attention due to its unique azepino­[5,4,3-cd]­indole framework. Herein, we report a novel biomimetic synthesis of clavicipitic acid diastereomers by utilizing a DDQ-mediated cross-dehydrogenative coupling (CDC) reaction....

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Bibliographic Details
Published inOrganic letters Vol. 25; no. 19; pp. 3456 - 3460
Main Authors Chiu, Kuei-Wei, Tseng, Yu-Hsun, Li, Ying-Xin, Chein, Rong-Jie
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.05.2023
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FORMAL SYNTHESIS
INDOLES
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Summary:Clavicipitic acid, a communesin alkaloid precursor, has attracted significant attention due to its unique azepino­[5,4,3-cd]­indole framework. Herein, we report a novel biomimetic synthesis of clavicipitic acid diastereomers by utilizing a DDQ-mediated cross-dehydrogenative coupling (CDC) reaction. The synthesis involves Suzuki coupling for the prenylation of a 4-bromotryptophan derivative, followed by an intramolecular CDC reaction to construct the azepinoindole core. The trans isomer was obtained as the major product, and the two diastereomers were separable. The CDC reaction conditions, including temperature, solvent, and protecting groups, were investigated, and a plausible mechanism for the observed diastereoselectivity was proposed.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c01029