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Issue 3, 2019
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Ciliatasecones A–C, three rearranged limonoids from Toona ciliata var. yunnanensis

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Abstract

Ciliatasecones A–C (1–3), three rearranged limonoids with a novel ring-seco model and an unprecedented cycle system, were isolated from the root bark of Toona ciliata var. yunnanensis. Ciliatasecones A–B (1–2) share a novel cyclopenta[b]furan ring C/D system through C-9/11-seco and C-11/14 ether linkage. Ciliatasecone C (3) was found to possess a rare rearranged six-membered lactone ring B between C-7 and C-9. Plausible biogenetic pathway speculation indicated that C-9/11 cleavage and oxygen bridge formation played the key roles in the framework rearrangement of 1–3.

Graphical abstract: Ciliatasecones A–C, three rearranged limonoids from Toona ciliata var. yunnanensis

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Publication details

The article was received on 04 Nov 2018, accepted on 10 Dec 2018 and first published on 11 Dec 2018


Article type: Paper
DOI: 10.1039/C8OB02736F
Citation: Org. Biomol. Chem., 2019,17, 555-560

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    Ciliatasecones A–C, three rearranged limonoids from Toona ciliata var. yunnanensis

    P. Zhang, Z. Cui, Y. Li, L. Heng, S. Wei, X. Wang, M. Yang, J. Luo and L. Kong, Org. Biomol. Chem., 2019, 17, 555
    DOI: 10.1039/C8OB02736F

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