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

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,...

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Bibliographic Details
Published in:Organic letters 2016-04, Vol.18 (8), p.1924-1927
Main Authors: 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
Format: Article
Language:English
Subjects:
Biochemical Phenomena
Circular Dichroism
Fruit
Limonins - chemical synthesis
Limonins - chemistry
Magnetic Resonance Spectroscopy
Meliaceae - chemistry
Molecular Structure
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b00738