Total synthesis and cytotoxicity of haterumalides NA and B and their artificial analogues

Mitsuru Ueda; Masashi Yamaura; Yoichi Ikeda; Yuta Suzuki; Kensaku Yoshizato; Ichiro Hayakawa; Hideo Kigoshi

doi:10.1021/jo802806z

Total synthesis and cytotoxicity of haterumalides NA and B and their artificial analogues

Mitsuru Ueda, Masashi Yamaura, Yoichi Ikeda, Yuta Suzuki, Kensaku Yoshizato, Ichiro Hayakawa, Hideo Kigoshi

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

31 Citations (Scopus)

Abstract

The total synthesis of haterumalides NA and B, potent cytotoxic marine macrolides, was achieved by using B-alkyl Suzuki-Miyaura coupling and Nozaki-Hiyama-Kishi coupling as key steps. Compared to our first-generation approach for enf-haterumalide NA methyl ester, this second-generation synthesis yielded much more of the key intermediate. This synthesis established the relative stereochemistry of haterumalide B. Furthermore, the structure-cytotoxicity relationships of haterumalides were investigated. The combination of macrolide and side chain parts proved to be important to the cytotoxicity.

Original language	English
Pages (from-to)	3370-3377
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	74
Issue number	9
DOIs	https://doi.org/10.1021/jo802806z
Publication status	Published - May 1 2009
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1021/jo802806z

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abstract = "The total synthesis of haterumalides NA and B, potent cytotoxic marine macrolides, was achieved by using B-alkyl Suzuki-Miyaura coupling and Nozaki-Hiyama-Kishi coupling as key steps. Compared to our first-generation approach for enf-haterumalide NA methyl ester, this second-generation synthesis yielded much more of the key intermediate. This synthesis established the relative stereochemistry of haterumalide B. Furthermore, the structure-cytotoxicity relationships of haterumalides were investigated. The combination of macrolide and side chain parts proved to be important to the cytotoxicity.",

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AU - Ueda, Mitsuru

AU - Yamaura, Masashi

AU - Ikeda, Yoichi

AU - Suzuki, Yuta

AU - Yoshizato, Kensaku

AU - Hayakawa, Ichiro

AU - Kigoshi, Hideo

PY - 2009/5/1

Y1 - 2009/5/1

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AB - The total synthesis of haterumalides NA and B, potent cytotoxic marine macrolides, was achieved by using B-alkyl Suzuki-Miyaura coupling and Nozaki-Hiyama-Kishi coupling as key steps. Compared to our first-generation approach for enf-haterumalide NA methyl ester, this second-generation synthesis yielded much more of the key intermediate. This synthesis established the relative stereochemistry of haterumalide B. Furthermore, the structure-cytotoxicity relationships of haterumalides were investigated. The combination of macrolide and side chain parts proved to be important to the cytotoxicity.

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Total synthesis and cytotoxicity of haterumalides NA and B and their artificial analogues

Abstract

ASJC Scopus subject areas

UN SDGs

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