Divergent total synthesis of penaresidin B and its straight side chain analogue

Tomoya Fujiwara; Kazuki Hashimoto; Masanori Umeda; Saki Murayama; Yuki Ohno; Bo Liu; Hisanori Nambu; Takayuki Yakura

doi:10.1016/j.tet.2018.07.023

Divergent total synthesis of penaresidin B and its straight side chain analogue

Tomoya Fujiwara, Kazuki Hashimoto, Masanori Umeda, Saki Murayama, Yuki Ohno, Bo Liu, Hisanori Nambu, Takayuki Yakura^*

^*この論文の責任著者

分子合成化学研究室

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

13 被引用数 (Scopus)

抄録

The divergent synthesis of penaresidin B and its straight side chain analogue was accomplished by constructing an azetidine ring via S_N2 type cyclization of protected 2,3-syn-3,4-syn-4-amino-1,3-dihydroxyhept-6-en-2-yl mesylate and late-stage introduction of an alkyl side chain via olefin cross-metathesis of 4-allylazetidine with readily available terminal alkenes. This synthetic route would be useful to synthesize penaresidin side chain analogues.

本文言語	英語
ページ（範囲）	4578-4591
ページ数	14
ジャーナル	Tetrahedron
巻	74
号	35
DOI	https://doi.org/10.1016/j.tet.2018.07.023
出版ステータス	出版済み - 2018/08/30

ASJC Scopus 主題領域

生化学
創薬
有機化学

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10.1016/j.tet.2018.07.023

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title = "Divergent total synthesis of penaresidin B and its straight side chain analogue",

abstract = "The divergent synthesis of penaresidin B and its straight side chain analogue was accomplished by constructing an azetidine ring via SN2 type cyclization of protected 2,3-syn-3,4-syn-4-amino-1,3-dihydroxyhept-6-en-2-yl mesylate and late-stage introduction of an alkyl side chain via olefin cross-metathesis of 4-allylazetidine with readily available terminal alkenes. This synthetic route would be useful to synthesize penaresidin side chain analogues.",

keywords = "Analogue, Azetidine, Olefin cross-metathesis reaction, Penaresidin, S2 cyclization",

author = "Tomoya Fujiwara and Kazuki Hashimoto and Masanori Umeda and Saki Murayama and Yuki Ohno and Bo Liu and Hisanori Nambu and Takayuki Yakura",

note = "Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",

year = "2018",

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day = "30",

doi = "10.1016/j.tet.2018.07.023",

language = "英語",

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T1 - Divergent total synthesis of penaresidin B and its straight side chain analogue

AU - Fujiwara, Tomoya

AU - Hashimoto, Kazuki

AU - Umeda, Masanori

AU - Murayama, Saki

AU - Ohno, Yuki

AU - Liu, Bo

AU - Nambu, Hisanori

AU - Yakura, Takayuki

PY - 2018/8/30

Y1 - 2018/8/30

N2 - The divergent synthesis of penaresidin B and its straight side chain analogue was accomplished by constructing an azetidine ring via SN2 type cyclization of protected 2,3-syn-3,4-syn-4-amino-1,3-dihydroxyhept-6-en-2-yl mesylate and late-stage introduction of an alkyl side chain via olefin cross-metathesis of 4-allylazetidine with readily available terminal alkenes. This synthetic route would be useful to synthesize penaresidin side chain analogues.

AB - The divergent synthesis of penaresidin B and its straight side chain analogue was accomplished by constructing an azetidine ring via SN2 type cyclization of protected 2,3-syn-3,4-syn-4-amino-1,3-dihydroxyhept-6-en-2-yl mesylate and late-stage introduction of an alkyl side chain via olefin cross-metathesis of 4-allylazetidine with readily available terminal alkenes. This synthetic route would be useful to synthesize penaresidin side chain analogues.

KW - Analogue

KW - Azetidine

KW - Olefin cross-metathesis reaction

KW - Penaresidin

KW - S2 cyclization

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U2 - 10.1016/j.tet.2018.07.023

DO - 10.1016/j.tet.2018.07.023

M3 - 学術論文

AN - SCOPUS:85050134960

SN - 0040-4020

VL - 74

SP - 4578

EP - 4591

JO - Tetrahedron

JF - Tetrahedron

IS - 35

ER -

Divergent total synthesis of penaresidin B and its straight side chain analogue

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