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^*

^*Corresponding author for this work

Synthetic and Biomolecular Organic Chemistry

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

13 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	4578-4591
Number of pages	14
Journal	Tetrahedron
Volume	74
Issue number	35
DOIs	https://doi.org/10.1016/j.tet.2018.07.023
State	Published - 2018/08/30

Keywords

Analogue
Azetidine
Olefin cross-metathesis reaction
Penaresidin
S2 cyclization

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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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",

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

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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

Abstract

Keywords

ASJC Scopus subject areas

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