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ChemInform Abstract: Structure and Biomimetic, Electrochemically-Mediated Semisynthesis of the Novel Pentacyclic Indole Danuphylline.

✍ Scribed by Toh-Seok Kam; Tuck-Meng Lim; Yeun-Mun Choo

Publisher: John Wiley and Sons
Year: 2010
Weight: 34 KB
Volume: 30
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199923250

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✦ Synopsis

Structure and Biomimetic, Electrochemically-Mediated Semisynthesis of the Novel Pentacyclic Indole Danuphylline.

-The structure of alkaloid (I), isolated in minor amounts from the leaf of Kopsia dasyrachis besides major alkaloid (II), is determined by spectroscopic means. Semisynthesis of compound (I) is achieved by anodic oxidation of alkaloid (II) until consumption of 2Fmol -1 of charge, followed by facile retro-aldol reaction of the intermediate iminium salt on silica gel chromatography. Allowing the oxidation to proceed until consumption of 4Fmol -of charge results in unprecedented chlorination, generating a mixture of chlorination products (IV) and (V). -

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