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

Ichiro Hayakawa; Hideo Kigoshi

doi:10.5059/yukigoseikyokaishi.68.814

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

Ichiro Hayakawa, Hideo Kigoshi

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

4 Citations (Scopus)

Abstract

Haterumalides, isolated from Okinawan marine animals, are 14-membered macrolides with strong cytotoxicity against human cancer cell lines. We have achieved the total synthesis of haterumalides NA and B by using B-alkyl Suzuki-Miyaura coupling and Nozaki-HiyamaKishi coupling as key steps. Compared to our first-generation approach for ent-haterumalide NA methyl ester, this second-generation synthesis yielded the key intermediate in much better yield. This synthesis also 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 strong cytotoxicity.

Original language	English
Pages (from-to)	814-823
Number of pages	10
Journal	Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume	68
Issue number	8
DOIs	https://doi.org/10.5059/yukigoseikyokaishi.68.814
Publication status	Published - Aug 1 2010
Externally published	Yes

Keywords

Biselides
Haterumalides
Marine cytotoxic macrolides
Structure-cytotoxicity relationships
Total synthesis

ASJC Scopus subject areas

Organic Chemistry

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abstract = "Haterumalides, isolated from Okinawan marine animals, are 14-membered macrolides with strong cytotoxicity against human cancer cell lines. We have achieved the total synthesis of haterumalides NA and B by using B-alkyl Suzuki-Miyaura coupling and Nozaki-HiyamaKishi coupling as key steps. Compared to our first-generation approach for ent-haterumalide NA methyl ester, this second-generation synthesis yielded the key intermediate in much better yield. This synthesis also 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 strong cytotoxicity.",

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AU - Kigoshi, Hideo

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N2 - Haterumalides, isolated from Okinawan marine animals, are 14-membered macrolides with strong cytotoxicity against human cancer cell lines. We have achieved the total synthesis of haterumalides NA and B by using B-alkyl Suzuki-Miyaura coupling and Nozaki-HiyamaKishi coupling as key steps. Compared to our first-generation approach for ent-haterumalide NA methyl ester, this second-generation synthesis yielded the key intermediate in much better yield. This synthesis also 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 strong cytotoxicity.

AB - Haterumalides, isolated from Okinawan marine animals, are 14-membered macrolides with strong cytotoxicity against human cancer cell lines. We have achieved the total synthesis of haterumalides NA and B by using B-alkyl Suzuki-Miyaura coupling and Nozaki-HiyamaKishi coupling as key steps. Compared to our first-generation approach for ent-haterumalide NA methyl ester, this second-generation synthesis yielded the key intermediate in much better yield. This synthesis also 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 strong cytotoxicity.

KW - Biselides

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KW - Structure-cytotoxicity relationships

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