Construction of the tetracyclic ring system of diterpene alkaloids cationic [5 + 2] cycloaddition

The ABCD ring system of C 18 /C 19 diterpene alkaloids was constructed via cationic [5 + 2] cycloaddition to forge a bicyclo[3.2.1]octane, an intramolecular aldol reaction to form a seven-membered ring, oxidation of a phenol at the para -position, and introduction of a one-carbon unit via Stille cou...

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Published inOrganic & biomolecular chemistry Vol. 21; no. 22; pp. 4587 - 459
Main Authors Mizuno, Kosuke, Nishiyama, Yoshitake, Yokoshima, Satoshi
Format Journal Article
Published 07.06.2023
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Summary:The ABCD ring system of C 18 /C 19 diterpene alkaloids was constructed via cationic [5 + 2] cycloaddition to forge a bicyclo[3.2.1]octane, an intramolecular aldol reaction to form a seven-membered ring, oxidation of a phenol at the para -position, and introduction of a one-carbon unit via Stille coupling followed by oxidative cleavage of a furan ring. The ABCD ring system of C 18 /C 19 diterpene alkaloids was constructed via cationic [5 + 2] cycloaddition and an intramolecular aldol reaction.
Bibliography:https://doi.org/10.1039/d3ob00647f
Electronic supplementary information (ESI) available. See DOI
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob00647f