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

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^*

^*Corresponding author for this work

Synthetic and Biomolecular Organic Chemistry

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

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.

Original language	English
Pages (from-to)	179-188
Number of pages	10
Journal	Chemical and Pharmaceutical Bulletin
Volume	64
Issue number	2
DOIs	https://doi.org/10.1248/cpb.c15-00816
State	Published - 2016/02/01

Keywords

Analogue
Olefin cross-metathesis reaction
Pachastrissamine
Stereoselective reduction

ASJC Scopus subject areas

General Chemistry
Drug Discovery

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title = "Practical synthesis of pachastrissamine (Jaspine B), 2-epi-pachastrissamine, and the 2-epi-pyrrolidine analogue",

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.",

keywords = "Analogue, Olefin cross-metathesis reaction, Pachastrissamine, Stereoselective reduction",

author = "Tomoya Fujiwara and Bo Liu and Wenqi Niu and Kazuki Hashimoto and Hisanori Nambu and Takayuki Yakura",

note = "Publisher Copyright: {\textcopyright} 2016 The Pharmaceutical Society of Japan.",

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T1 - Practical synthesis of pachastrissamine (Jaspine B), 2-epi-pachastrissamine, and the 2-epi-pyrrolidine analogue

AU - Fujiwara, Tomoya

AU - Liu, Bo

AU - Niu, Wenqi

AU - Hashimoto, Kazuki

AU - Nambu, Hisanori

AU - Yakura, Takayuki

PY - 2016/2/1

Y1 - 2016/2/1

N2 - 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.

AB - 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.

KW - Analogue

KW - Olefin cross-metathesis reaction

KW - Pachastrissamine

KW - Stereoselective reduction

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AN - SCOPUS:84958177008

SN - 0009-2363

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SP - 179

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JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

IS - 2

ER -

Practical synthesis of pachastrissamine (Jaspine B), 2-epi-pachastrissamine, and the 2-epi-pyrrolidine analogue

Abstract

Keywords

ASJC Scopus subject areas

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