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(8H)‐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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Jefford et al. (1986) studied this question.
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