Issue 12, 2017

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
02 aug 2017
Accepted
05 sep 2017
First published
06 sep 2017

Org. Chem. Front., 2017,4, 2417-2421

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, 4, 2417 DOI: 10.1039/C7QO00678K

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