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Communication | Special issue | Vol 66, No. 1, 2005, pp.181-185
Published online, 15th November, 2005
DOI: 10.3987/COM-05-S(K)71
Diastereoselective Fischer-Type Pyrroloindole Synthesis and Its Application to the Synthesis of Chiral Pyrroloindole Alkaloids

Atsushi Nishida,* Satoru Ushigome, Ayako Sugimoto, and Shigeru Arai

*Graduate School of Pharmaceutical Science, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

Abstract

Facile access to optically active pyrroloindoles by Fischer-type pyrroloindole synthesis is investigated. The reaction using chiral hydrazines prepared from commercially available chiral amines proceeded with diastereoselective cyclization (up to 70% de), and a short-step conversion of the cycloadducts to (-)-desoxyeseroline and pyrroloindole alkaloids was achieved.