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Communication | Special issue | Vol 67, No. 1, 2006, pp.89-93
Published online, 6th September, 2005
DOI: 10.3987/COM-05-S(T)21
Ruthenium-catalyzed ROM-RCM of Cyclopentene-yne. Concise Synthesis of a Pyrrolizidine Derivative

Hideaki Wakamatsu, Yoshihiro Sato, Reiko Fujita,* and Miwako Mori*

*Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12 Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan

Abstract

ROM-RCM (Ring-Opening Metathesis and Ring-Closing Metathesis) of cyclopentene-yne having an ester moiety was demonstrated using first- and second-generation Grubbs’ catalysts. When the reaction of cycloalkene-yne was carried out in the presence of 5 mol % of a ruthenium carbene complex under ethylene atmosphere at room temperature, ROM-RCM proceeded smoothly to give a pyrrolidine derivative in good yield, which could be converted to a pyrrolizidine derivative.