Issue 6, 2018

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
05 دسمبر 2017
Accepted
07 جنؤری 2018
First published
08 جنؤری 2018

Org. Chem. Front., 2018,5, 1022-1027

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements