Concise synthesis of anticancer active trans-4-(4-Octylphenyl)prolinol

Junki Ando; Aoi Tazawa; Kohei Ishizawa; Minoru Tanaka; Hiroyoshi Takamura

doi:10.3987/COM-18-S(F)44

Concise synthesis of anticancer active trans-4-(4-Octylphenyl)prolinol

Junki Ando, Aoi Tazawa, Kohei Ishizawa, Minoru Tanaka, Hiroyoshi Takamura

School of Science

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

Abstract

Concise synthesis of anticancer active trans-4-(4-octylphenyl)prolinol has been achieved. Regioselective iodination of aromatic compound and subsequent Suzuki-Miyaura cross-coupling with trans-1-octen-1-ylboronic acid produced the desired coupling product. Further transformation of this product afforded trans-4-(4-octylphenyl)prolinol. The synthesis of this anticancer compound has been performed with 23% overall yield and six steps, which have been improved in comparison with those (3.5% overall yield and eight steps) previously reported.

Original language	English
Pages (from-to)	716-723
Number of pages	8
Journal	Heterocycles
Volume	99
Issue number	1
DOIs	https://doi.org/10.3987/COM-18-S(F)44
Publication status	Published - 2019

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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title = "Concise synthesis of anticancer active trans-4-(4-Octylphenyl)prolinol",

abstract = "Concise synthesis of anticancer active trans-4-(4-octylphenyl)prolinol has been achieved. Regioselective iodination of aromatic compound and subsequent Suzuki-Miyaura cross-coupling with trans-1-octen-1-ylboronic acid produced the desired coupling product. Further transformation of this product afforded trans-4-(4-octylphenyl)prolinol. The synthesis of this anticancer compound has been performed with 23% overall yield and six steps, which have been improved in comparison with those (3.5% overall yield and eight steps) previously reported.",

author = "Junki Ando and Aoi Tazawa and Kohei Ishizawa and Minoru Tanaka and Hiroyoshi Takamura",

note = "Funding Information: We thank Dr. Masayuki Watanabe, Mr. Kazunari Shimooka, and Ms. Kaoru Marukawa for valuable discussions. We also thank Ms. Kaori Murakoshi for technical support of LC-MS/MS analysis, Ms. Saori Tahara for technical support of IR analysis, and Mr. Iwao Takamuro for helpful advice. This research was supported by Mitsubishi Tanabe Pharma Corporation. Publisher Copyright: {\textcopyright} 2019 The Japan Institute of Heterocyclic Chemistry.",

year = "2019",

doi = "10.3987/COM-18-S(F)44",

language = "English",

volume = "99",

pages = "716--723",

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publisher = "Japan Institute of Heterocyclic Chemistry",

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T1 - Concise synthesis of anticancer active trans-4-(4-Octylphenyl)prolinol

AU - Ando, Junki

AU - Tazawa, Aoi

AU - Ishizawa, Kohei

AU - Tanaka, Minoru

AU - Takamura, Hiroyoshi

N1 - Funding Information: We thank Dr. Masayuki Watanabe, Mr. Kazunari Shimooka, and Ms. Kaoru Marukawa for valuable discussions. We also thank Ms. Kaori Murakoshi for technical support of LC-MS/MS analysis, Ms. Saori Tahara for technical support of IR analysis, and Mr. Iwao Takamuro for helpful advice. This research was supported by Mitsubishi Tanabe Pharma Corporation. Publisher Copyright: © 2019 The Japan Institute of Heterocyclic Chemistry.

PY - 2019

Y1 - 2019

N2 - Concise synthesis of anticancer active trans-4-(4-octylphenyl)prolinol has been achieved. Regioselective iodination of aromatic compound and subsequent Suzuki-Miyaura cross-coupling with trans-1-octen-1-ylboronic acid produced the desired coupling product. Further transformation of this product afforded trans-4-(4-octylphenyl)prolinol. The synthesis of this anticancer compound has been performed with 23% overall yield and six steps, which have been improved in comparison with those (3.5% overall yield and eight steps) previously reported.

AB - Concise synthesis of anticancer active trans-4-(4-octylphenyl)prolinol has been achieved. Regioselective iodination of aromatic compound and subsequent Suzuki-Miyaura cross-coupling with trans-1-octen-1-ylboronic acid produced the desired coupling product. Further transformation of this product afforded trans-4-(4-octylphenyl)prolinol. The synthesis of this anticancer compound has been performed with 23% overall yield and six steps, which have been improved in comparison with those (3.5% overall yield and eight steps) previously reported.

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Concise synthesis of anticancer active trans-4-(4-Octylphenyl)prolinol

Abstract

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