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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
New azaphilones from the inedible mushroom Hypoxylon rubiginosum
Dang Ngoc Quang1, Toshihiro Hashimoto, Marc Stadler
1Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan.
Abstract:
Fractionation of the methanol extract of the fruit bodies of the xylariaceus ascomycete Hypoxylon rubiginosum resulted in the isolation of three new azaphilone derivatives named rubiginosins A-C (1-3) and a new fatty acid named rubiginosic acid (4), together with three known compounds, entonaemin A (5), daldinin C (6), and orsellinic acid. Their structures were elucidated by 2D NMR, MS, IR, and UV spectra and chemical reaction. The absolute configuration of compound 3 was established by CD spectroscopy. The structure of 4 was confirmed by X-ray crystallographic analysis.
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Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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