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Paper | Regular issue | Vol 48, No. 8, 1998, pp.1599-1607
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8213
General Method for Synthesis of Erythrinan and Homoerythrinan Alkaloids (2): Application of Pummerer-Type Reaction to the Synthesis of Homoerythrinan Ring System

Jun Toda, Yoshihiro Niimura, Takehiro Sano,* and Yoshisuke Tsuda

*Showa Pharmaceutical University, 3-3165, Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan


The sythesis of cyclohomoerythrinan (2a), a potential intermediate to homoerythrinan alkaloids, was achieved by a Pummerer-Type cyclization of the hydroindole sulfoxide (11), which was prepared from the dioxopyrroline (6) in five steps via a [2+2] photocycloaddition reaction followed by an anionic 1,3-shift.