Cyclobutane-Containing Meroditerpenoids, (+)-Isoscopariusins B and C: Structure Elucidation and Biomimetic Synthesis

(+)-Isoscopariusins B (1) and C (2), two meroditerpenoids containing a 6/6/4 tricyclic carbon skeleton and seven continuous stereocenters, were identified from Isodon scoparius. The structures were determined by nuclear magnetic resonance analysis and concise biomimetic syntheses from readily availa...

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Veröffentlicht in:Organic letters 2023-05, Vol.25 (17), p.2981-2985
Hauptverfasser: Li, Ming-Xiang, Yan, Bing-Chao, Zhou, Min, Li, Xing-Ren, Li, Xiao-nian, He, Shi-Jun, Sun, Han-Dong, Puno, Pema-Tenzin
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Sprache:eng
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Zusammenfassung:(+)-Isoscopariusins B (1) and C (2), two meroditerpenoids containing a 6/6/4 tricyclic carbon skeleton and seven continuous stereocenters, were identified from Isodon scoparius. The structures were determined by nuclear magnetic resonance analysis and concise biomimetic syntheses from readily available alkene 5 in seven and six steps, respectively. An intermolecular [2+2] photocycloaddition with cooperative catalysis of a Lewis acid and an Ir photocatalyst was used to construct a cyclobutane core with four stereogenic centers.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c00742