Spirotrichilins A and B: Two Rearranged Spirocyclic Limonoids from Trichilia connaroides

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 and B: Two Rearranged Spirocyclic Limonoids from Trichilia connaroides

2016

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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