Practical Synthesis of Pachastrissamine (Jaspine B), 2-epi-Pachastrissamine, and the 2-epi-Pyrrolidine Analogue

Tomoya Fujiwara; Bo Liu; Wenqi Niu; Kazuki Hashimoto; Hisanori Nambu; Takayuki Yakura

doi:10.1248/cpb.c15-00816

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Practical Synthesis of Pachastrissamine (Jaspine B), 2-epi-Pachastrissamine, and the 2-epi-Pyrrolidine Analogue

Tomoya Fujiwara, Bo Liu, Wenqi Niu, Kazuki Hashimoto, Hisanori Nambu, Takayuki Yakura

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Keywords: pachastrissamine, analogue, stereoselective reduction, olefin cross-metathesis reaction

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2016 Volume 64 Issue 2 Pages 179-188

DOI https://doi.org/10.1248/cpb.c15-00816

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Abstract

The practical syntheses of pachastrissamine (jaspine B), 2-epi-pachastrissamine, and the 2-epimer of the pyrrolidine analogue were accomplished via the stereoselective reduction of an allylketone derived from commercially available diethyl D-tartrate and the cross-metathesis of an allyltetrahydrofuran or allypyrrolidine with 1-tridecene as key steps.

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