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■ Samarium(II) Iodide-mediated Intramolecular Aldol-type Cyclization

Masakazu Sono, Yasuyo Nakashiba, Katsuyuki Nakashima, Shigeru Takaoka, and Motoo Tori*

*Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-machi, Tokushima, 770-8514, Japan

Abstract

The α-substituted α,β-epoxy ketone having a formyl group in the molecule reacted with samarium(II) iodide to afford cyclized spiro ketones formed by an intramolecular aldol-type reaction. However, in the presence of proton source the ratio of spiro products decreased and the yield of hydrindanone increased. The α-substituted α,β-unsaturated cyclopentenone derivative smoothly cyclized into the same hydrindanone.