Related Experiment Video
Updated: Dec 23, 2025

Biosynthesis of a Flavonol from a Flavanone by Establishing a One-pot Bienzymatic Cascade
Published on: August 14, 2019
Total Synthesis of Sophoraflavanone H and Confirmation of Its Absolute Configuration
Haruka Murakami1, Tomohiro Asakawa1,2, Yoshihiro Muramatsu1
1School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga, Shizuoka, Shizuoka 422-8526, Japan.
Abstract:
Sophoraflavanone H (1) is a polyphenol with a hybrid-type structure containing 2,3-diaryl-2,3-dihydrobenzofuran and flavanone ring moieties. This compound and related analogues are promising leads for antimicrobial and antitumor drug development. Here we describe a total synthesis of 1 and its diastereomer. The dihydrobenzofuran and flavanone rings were constructed by a Rh-catalyzed asymmetric C-H insertion reaction and selective oxy-Michael reaction. The absolute configuration of 1 was established by X-ray crystallographic analysis and CD spectral investigation of synthetic derivatives.
Related Concept Videos
Aromatic Hydrocarbon Anions: Structural Overview
Due to the absence of continuous...
Stereoisomerism of Cyclic Compounds
Conformations of Cyclohexane
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal...
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
Molecules with Multiple Chiral Centers
Stereoisomerism
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...

