Intramolecular Carbenoid Reactions of Pyrrole Derivatives. A Total Synthesis of (±)‐Ipalbidine | Zendy

Jefford Charles W. | Zendy; Kubota Tadatoshi | Zendy; Zaslona Alexander | Zendy

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Intramolecular Carbenoid Reactions of Pyrrole Derivatives. A Total Synthesis of (±)‐Ipalbidine

Author(s) -

Jefford Charles W.,

Kubota Tadatoshi,

Zaslona Alexander

Publication year - 1986

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19860690828

Subject(s) - carbenoid , chemistry , intramolecular force , yield (engineering) , total synthesis , pyrrole , medicinal chemistry , diazo , intramolecular reaction , decomposition , rhodium , organic chemistry , stereochemistry , catalysis , materials science , metallurgy

A new method for alkaloid synthesis is described. The rhodium(II)‐acetate‐catalyzed decomposition of 3‐(4‐acetoxyphenyl)‐1‐diazo‐4‐(pyrrol‐1‐yl)‐2‐butanone ( 5d ) gave 6‐(4‐acetoxyphenyl)‐5,6‐dihydro‐7(8 H )‐indolizinone ( 6d ) in 82% yield via an intramolecular carbenoid reaction. The latter compound was converted in four steps in 13% overall yield to (±)‐ipalbidine ( 1b ).

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