Determination of the Absolute Configuration of Super-Carbon-Chain Compounds by a Combined Chemical, Spectroscopic, and Computational Approach: Gibbosols A and B

Li, Wan-Shan and Yan, Ren-Jie and Yu, Yi and Shi, Zhi and Mándi, Attila and Shen, Li and Kurtán, Tibor and Wu, Jun (2020) Determination of the Absolute Configuration of Super-Carbon-Chain Compounds by a Combined Chemical, Spectroscopic, and Computational Approach: Gibbosols A and B. ANGEWANDTE CHEMIE INTERNATIONAL EDITION, 59 (31). pp. 13028-13036. ISSN 1433-7851

Text AngewChemIntEd_2020_59_13028_LiWS.pdf Restricted to Registered users only Download (4MB)

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.

Actions (login required)

Edit Item