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Communication | Special issue | Vol 79, No. 1, 2009, pp.433-439
Published online, 26th December, 2008
DOI: 10.3987/COM-08-S(D)75
New Entry to the Asymmetric Synthesis of (–)-Lasubine I and (+)-Subcosine I

Naoki Yamazaki,* Masakazu Atobe, Chihiro Kibayashi, and Sakae Aoyagi*

*Faculty of Pharmaceutical Science, Iwaki Meisei University, , Japan

Abstract

A new synthetic entry to (–)-lasubine I and (+)-subcosine I has been established by employing the (S)-allylalkoxy benzylamine as a chiral synthon. The synthesis involves the formation of an α,β-unsaturated lactone by RCM reaction followed by an intramolecular Michael-type addition reaction as a key step, which enables the stereoselective construction of the cis-quinolizidine skeleton of lasubine I and subcosine I.