Dioxopyrrolines. XLIII. : Diels-Alder Reaction of 4, 5-Diethoxycarbonyl-1H-pyrrole-2, 3-dione with Butadienes : Synthesis of Polyfunctionalized Hydroindoles

Kimiaki ISOBE; Chie MOHRI; Hiromichi SANO; Kunihiko MOHRI; Hiroshi ENOMOTO; Takehiro SANO; Yoshisuke TSUDA

doi:10.1248/cpb.37.3236

Kimiaki ISOBE, Chie MOHRI, Hiromichi SANO, Kunihiko MOHRI, Hiroshi ENOMOTO, Takehiro SANO, Yoshisuke TSUDA

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Keywords: dioxopyrroline, 4, 5-diethoxycarbonyl-1H-pyrrole-2, 3-dione, dienophile, butadiene, 2, 3-bis(trimethylsilyloxy)-butadiene, 1-methoxybutadiene, 1-sulfenylbutadiene, 2-trimethylsilyloxy-butadiene, Diels-Alder reaction, hydroindole

JOURNAL FREE ACCESS

1989 Volume 37 Issue 12 Pages 3236-3238

DOI https://doi.org/10.1248/cpb.37.3236

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Abstract

A new dioxopyrroline, 4, 5-diethoxycarbonyl-1H-pyrrole-2, 3-dione (3), was proved to be a strong dienophile in the Diels-Alder reaction with various butadienes. This cycloaddition reaction proceeded in a regio- and stereo-selective manner to give the polyfunctionalized hydroindoles (4-8, 10) which may be potential synthetic intermediates of Erythrina alkaloids.

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