Total synthesis of nitropyrrolins A, B, and D

Hikaru Mitani; Tomoki Matsuo; Takeshi Kodama; Keisuke Nishikawa; Yoshimitsu Tachi; Yoshiki Morimoto

doi:10.1016/j.tet.2016.09.058

Total synthesis of nitropyrrolins A, B, and D

Hikaru Mitani, Tomoki Matsuo, Takeshi Kodama, Keisuke Nishikawa, Yoshimitsu Tachi, Yoshiki Morimoto^*

^*Corresponding author for this work

Section of Natural Products & Drug Discovery, Division of Medicinal Resources, Institute of Natural Medicine

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

6 Scopus citations

Abstract

The chemical synthetic method of cytotoxic nitropyrrolins A (1), B (2), and D (4), 2-nitropyrrole terpenoids rarely occurring in nature, has been developed for further biological studies. After the synthesis of nitropyrrolin B has first been achieved, nitropyrrolin B was transformed into nitropyrrolins A and D in two steps and one step, respectively. The regio- and stereoselective epoxide-cleavage reaction was highlighted in the direct conversion of nitropyrrolin B to D.

Original language	English
Pages (from-to)	7179-7184
Number of pages	6
Journal	Tetrahedron
Volume	72
Issue number	45
DOIs	https://doi.org/10.1016/j.tet.2016.09.058
State	Published - 2016

Keywords

4-Farnesylated-2-nitropyrrole
Cytotoxicity
Epoxide-cleavage reaction
Nitropyrrolins A, B, and D
Total synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Total synthesis of nitropyrrolins A, B, and D",

abstract = "The chemical synthetic method of cytotoxic nitropyrrolins A (1), B (2), and D (4), 2-nitropyrrole terpenoids rarely occurring in nature, has been developed for further biological studies. After the synthesis of nitropyrrolin B has first been achieved, nitropyrrolin B was transformed into nitropyrrolins A and D in two steps and one step, respectively. The regio- and stereoselective epoxide-cleavage reaction was highlighted in the direct conversion of nitropyrrolin B to D.",

keywords = "4-Farnesylated-2-nitropyrrole, Cytotoxicity, Epoxide-cleavage reaction, Nitropyrrolins A, B, and D, Total synthesis",

author = "Hikaru Mitani and Tomoki Matsuo and Takeshi Kodama and Keisuke Nishikawa and Yoshimitsu Tachi and Yoshiki Morimoto",

note = "Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd",

year = "2016",

doi = "10.1016/j.tet.2016.09.058",

language = "英語",

volume = "72",

pages = "7179--7184",

journal = "Tetrahedron",

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TY - JOUR

T1 - Total synthesis of nitropyrrolins A, B, and D

AU - Mitani, Hikaru

AU - Matsuo, Tomoki

AU - Kodama, Takeshi

AU - Nishikawa, Keisuke

AU - Tachi, Yoshimitsu

AU - Morimoto, Yoshiki

PY - 2016

Y1 - 2016

N2 - The chemical synthetic method of cytotoxic nitropyrrolins A (1), B (2), and D (4), 2-nitropyrrole terpenoids rarely occurring in nature, has been developed for further biological studies. After the synthesis of nitropyrrolin B has first been achieved, nitropyrrolin B was transformed into nitropyrrolins A and D in two steps and one step, respectively. The regio- and stereoselective epoxide-cleavage reaction was highlighted in the direct conversion of nitropyrrolin B to D.

AB - The chemical synthetic method of cytotoxic nitropyrrolins A (1), B (2), and D (4), 2-nitropyrrole terpenoids rarely occurring in nature, has been developed for further biological studies. After the synthesis of nitropyrrolin B has first been achieved, nitropyrrolin B was transformed into nitropyrrolins A and D in two steps and one step, respectively. The regio- and stereoselective epoxide-cleavage reaction was highlighted in the direct conversion of nitropyrrolin B to D.

KW - 4-Farnesylated-2-nitropyrrole

KW - Cytotoxicity

KW - Epoxide-cleavage reaction

KW - Nitropyrrolins A, B, and D

KW - Total synthesis

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U2 - 10.1016/j.tet.2016.09.058

DO - 10.1016/j.tet.2016.09.058

M3 - 学術論文

AN - SCOPUS:84991573076

SN - 0040-4020

VL - 72

SP - 7179

EP - 7184

JO - Tetrahedron

JF - Tetrahedron

IS - 45

ER -

Total synthesis of nitropyrrolins A, B, and D

Abstract

Keywords

ASJC Scopus subject areas

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