Sweritranslactones A–C: Unusual Skeleton Secoiridoid Dimers via [4 + 2] Cycloaddition from Swertiamarin

Skeleton-diversity-oriented chemical conversion from pure natural products is a valuable method to obtain natural product-like compounds, especially those with novel architecture. The application of phytochemical methods to iridoids yielded three novel secoiridoid dimers: sweritranslactones A–C (1–3...

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Bibliographic Details
Published in:Journal of organic chemistry 2017-12, Vol.82 (24), p.13263-13267
Main Authors: Liu, Lu, Xu, Guan-Ling, Ma, Xiao-Xia, Khan, Afsar, Tan, Wen-Hong, Yang, Zhu-Ya, Zhou, Zhi-Hong
Format: Article
Language:English
Subjects:
Crystallography, X-Ray
Cycloaddition Reaction
Dimerization
Iridoid Glucosides - chemistry
Iridoids - chemistry
Molecular Structure
Pyrones - chemistry
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Summary:Skeleton-diversity-oriented chemical conversion from pure natural products is a valuable method to obtain natural product-like compounds, especially those with novel architecture. The application of phytochemical methods to iridoids yielded three novel secoiridoid dimers: sweritranslactones A–C (1–3). These molecules possess a 6/6/6/6/6/6-fused hexacyclic skeleton and were obtained from swertiamarin, one of the major constituents of the genus Swertia, via a [4 + 2] cycloaddition and intramolecular nucleophilic addition under aqueous conditions. The structures were established based on extensive spectroscopic characterization and X-ray crystallographic diffraction analysis.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b02383