Spirotrichilins A and B: Two Rearranged Spirocyclic Limonoids from Trichilia connaroides
2016
An, Fa-Liang | Luo, Jun | Li, Rui-Jun | Luo, Jian-Guang | Wang, Xiao-Bing | Yang, Ming-Hua | Yang, Lei | Yao, He-Quan | Sun, Hong-Bin | Chen, Yi-Jun | Kong, Ling-Yi
Spirotrichilins A (1) and B (2), two novel limonoids with an unprecedented spiro[cyclopenta[b]furan-2,1′-cyclopentan] ring system in A/B/C rings, were isolated from the fruits of trichilia connaroides. Their planar structures and absolute configurations were established based on 1D-, 2D-NMR data, electronic circular dichroism (ECD) exciton chirality method and time-dependent density functional theory (TDDFT)/ECD calculation. A benzilic acid-like rearrangement in ring A was proposed as the key step in the plausible biogenetic pathway of 1 and 2.
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