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 journalArticle

26 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 languageEnglish
Pages (from-to)3370-3377
Number of pages8
JournalJournal of Organic Chemistry
Volume74
Issue number9
DOIs
Publication statusPublished - May 1 2009
Externally publishedYes

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Cytotoxicity
Macrolides
Stereochemistry
Esters

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Total synthesis and cytotoxicity of haterumalides NA and B and their artificial analogues. / Ueda, Mitsuru; Yamaura, Masashi; Ikeda, Yoichi; Suzuki, Yuta; Yoshizato, Kensaku; Hayakawa, Ichiro; Kigoshi, Hideo.

In: Journal of Organic Chemistry, Vol. 74, No. 9, 01.05.2009, p. 3370-3377.

Research output: Contribution to journalArticle

Ueda, M, Yamaura, M, Ikeda, Y, Suzuki, Y, Yoshizato, K, Hayakawa, I & Kigoshi, H 2009, 'Total synthesis and cytotoxicity of haterumalides NA and B and their artificial analogues', Journal of Organic Chemistry, vol. 74, no. 9, pp. 3370-3377. https://doi.org/10.1021/jo802806z
Ueda, Mitsuru ; Yamaura, Masashi ; Ikeda, Yoichi ; Suzuki, Yuta ; Yoshizato, Kensaku ; Hayakawa, Ichiro ; Kigoshi, Hideo. / Total synthesis and cytotoxicity of haterumalides NA and B and their artificial analogues. In: Journal of Organic Chemistry. 2009 ; Vol. 74, No. 9. pp. 3370-3377.
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