Design and Synthesis of Optically Pure Dibenzo-difuso-azacentrotriquinacene-based Pseudo-C2-Symmetric Cyclic Hydroxamic Acid

Cyclic hydroxamic acids are found in various natural products and bioactive compounds, which exhibit various bioactivities, such as HDAC inhibition and MMP inhibition. Furthermore, they have relatively high metal binding ability, therefore they can form various metal-complexes. Herein, we report des...

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Bibliographic Details
Published in:Chemistry letters 2019, Vol.48 (11), p.1328-1331
Main Authors: Ohtsuka, Naoya, Seki, Masato, Hoshino, Yujiro, Honda, Kiyoshi
Format: Article
Language:English
Subjects:
Biological activity
Coordination compounds
Crystal structure
Natural products
Oxidation
Palladium
Recrystallization
Synthesis
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Summary:Cyclic hydroxamic acids are found in various natural products and bioactive compounds, which exhibit various bioactivities, such as HDAC inhibition and MMP inhibition. Furthermore, they have relatively high metal binding ability, therefore they can form various metal-complexes. Herein, we report design, synthesis and optical resolution of dibenzo-difuso-azacentrotriquinacene-based chiral cyclic hydroxamic acid (CHA). CHA was synthesized from dibenzosuberenone over 16 steps in 11% overall yield, including triflation of enol followed by reduction of triflates using Pd catalyst and oxidation of amide with MoO5·2DMF as key steps. The optical resolution was achieved by recrystallization, and the structure and absolute configuration were determined by X-ray crystal analysis.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.190592