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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 ).