Premium
Determination of the Absolute Configuration of Super‐Carbon‐Chain Compounds by a Combined Chemical, Spectroscopic, and Computational Approach: Gibbosols A and B
Author(s) -
Li WanShan,
Yan RenJie,
Yu Yi,
Shi Zhi,
Mándi Attila,
Shen Li,
Kurtán Tibor,
Wu Jun
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202004358
Subject(s) - stereocenter , polyol , carbon chain , absolute configuration , carbon fibers , chemistry , molecule , chain (unit) , stereochemistry , asymmetric carbon , absolute (philosophy) , reinforced carbon–carbon , organic chemistry , materials science , enantioselective synthesis , alkyl , physics , catalysis , composite material , astronomy , composite number , philosophy , epistemology , polyurethane
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 C 69 ‐ or C 71 ‐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.