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Rearranged limonoids with unique 6/5/6/5 tetracarbocyclic skeletons from Toona ciliata and biomimetic structure divergence

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Abstract

Tooniliatone A (1), a novel limonoid with an unprecedented 6/5/6/5 tetracarbocyclic skeleton was isolated from Toona ciliata Roem. var. yunnanensis. Its rearranged ring-seco backbone was proposed to biosynthetically originate from co-isolated known toonacilin (3) via a rare electron-deficient alkene electrophilic cyclization and 1,2-alkyl shift sequence. The acid-catalyzed biomimetic conversion of 3 not only successfully afforded 1 but also another novel 6/5/6/5 tetracarbocyclic skeleton, tooniliatone B (2). The priority of 2 in this biomimetic conversion, the existence of 1 and the absence of 2 in the crude extract suggested the biosynthetic selectivity of 1 from 3. The divergent biomimetic sequence, based on a carbocation from an epoxide moiety, provided an inspiration for constructing complex polycyclic carbon skeletons.

Graphical abstract: Rearranged limonoids with unique 6/5/6/5 tetracarbocyclic skeletons from Toona ciliata and biomimetic structure divergence

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Publication details

The article was received on 02 Aug 2017, accepted on 05 Sep 2017 and first published on 06 Sep 2017


Article type: Research Article
DOI: 10.1039/C7QO00678K
Citation: Org. Chem. Front., 2017, Advance Article
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    Rearranged limonoids with unique 6/5/6/5 tetracarbocyclic skeletons from Toona ciliata and biomimetic structure divergence

    J. Luo, W. Huang, S. Hu, P. Zhang, X. Zhou, X. Wang, M. Yang, J. Luo, C. Wang, C. Liu, H. Yao, C. Zhang, H. Sun, Y. Chen and L. Kong, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00678K

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