Determination of the Absolute Configuration of Super-Carbon-Chain Compounds by a Combined Chemical, Spectroscopic, and Computational Approach: Gibbosols A and B
In memory of Professor Koji Nakanishi
Graphical 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.
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.
Conflict of interest
The authors declare no conflict of interest.
