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Paper | Special issue | Vol 84, No. 2, 2012, pp.929-944
Published online, 15th August, 2011
DOI: 10.3987/COM-11-S(P)74
Asymmetric Synthesis of 2-Propylisofagomine Using Allylic Hydroxy Group Accelerated Ring-Closing Enyne Metathesis

Tatsuya Taguchi, Tatsushi Imahori, Yuichi Yoshimura, Atsushi Kato, Isao Adachi, Masatoshi Kawahata, Kentaro Yamaguchi, and Hiroki Takahata*

*Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan

Abstract

An asymmetric synthesis of 2-propylisofagomine 5 using allylic hydroxy group accelerated ring-closing enyne metathesis (AHA-RCEM) was conducted with high diastereoselectivity in 13% overall yield starting from the commercially available (E)-hex-2-ol.