Racemic trinorsesquiterpenoids from the Beihai sponge Spongia officinalis: structure and biomimetic total synthesis
Literature Information
Publication Date
2018-01-08
DOI
10.1039/C7QO01091E
Impact Factor
5.281
Authors
Na-Na Yang, Le-Fu Lan, Xu-Wen Li
View Original
Abstract
Two rare new furan butanolides, namely sponalisolides A (1) and B (2), characterized by an unprecedented furan-bearing trinorsesquiterpene alkyl chain connecting either a butanolide (1) or an N-acyl homoserine lactone moiety (2), were isolated in racemic forms from the Beihai sponge Spongia officinalis, and were further separated, by chiral-phase HPLC, to their corresponding enantiomers 1a/1b and 2a/2b, respectively. The structures, including the absolute stereochemistry, of the two pairs of enantiomeric compounds, were unambiguously established by extensive spectroscopic analysis and biomimetic total synthesis, involving a key Johnson-Claisen rearrangement and a lactone cyclization after epoxidation or dihydroxylation. All the new compounds exhibited the Pseudomonas aeruginosa quorum sensing inhibitory activity.
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Organic Chemistry Frontiers
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Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
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