Determination of the Absolute Configuration of Super‐Carbon‐Chain Compounds by a Combined Chemical, Spectroscopic, and Computational Approach: Gibbosols A and B. Issue 31 (3rd June 2020)

• Record Type: Journal Article
• Authors: Li, Wan‐Shan; Yan, Ren‐Jie; Yu, Yi; Shi, Zhi; Mándi, Attila; Shen, Li; Kurtán, Tibor; Wu, Jun
• Is Part Of: Angewandte Chemie international edition. Volume 59:Issue 31(2020)
• Page Start: 13028
• Page End: 13036
• Publication Date: 2020-06-03
• Subjects: chain structures -- configuration determination -- natural products -- NMR spectroscopy -- structure elucidation; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.202004358
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Marine dinoflagellates produce remarkable organic molecules, particularly those with polyoxygenated long‐carbon‐chain backbones, namely super‐carbon‐chain compounds (SCCCs), characterized by the presence of numerous stereogenic carbon centers on acyclic polyol carbon chains. Even today, it is a challenge to determine the absolute configurations of these compounds. In this work, the planar structures and absolute configurations of two highly flexible SCCCs, featuring either a C69 ‐ or C71 ‐linear carbon backbone, gibbosols A and B, respectively, each containing thirty‐seven stereogenic carbon centers, were unambiguously established by a combined chemical, spectroscopic, and computational approach. The discovery of gibbosols A and B with two hydrophilic acyclic polyol chains represents an unprecedented class of SCCCs. A reasonable convergent strategy for the biosynthesis of these SCCCs was proposed. Abstract : Super‐carbon‐chain compounds : Gibbosols A and B, obtained from the South China Sea dinoflagellate Amphidinium gibbosum, are stereochemically challenging, flexible super‐carbon‐chain compounds. A combined chemical, spectroscopic, and computational approach was successfully employed to establish the absolute configurations of thirty‐seven stereogenic carbon centers within these structurally intriguing marine natural products.