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Issue 6, 2018
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Racemic trinorsesquiterpenoids from the Beihai sponge Spongia officinalis: structure and biomimetic total synthesis

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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.

Graphical abstract: Racemic trinorsesquiterpenoids from the Beihai sponge Spongia officinalis: structure and biomimetic total synthesis

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Publication details

The article was received on 05 Dec 2017, accepted on 07 Jan 2018 and first published on 08 Jan 2018


Article type: Research Article
DOI: 10.1039/C7QO01091E
Citation: Org. Chem. Front., 2018,5, 1022-1027
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    Racemic trinorsesquiterpenoids from the Beihai sponge Spongia officinalis: structure and biomimetic total synthesis

    D. Sun, G. Han, N. Yang, L. Lan, X. Li and Y. Guo, Org. Chem. Front., 2018, 5, 1022
    DOI: 10.1039/C7QO01091E

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