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

27 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

ASJC Scopus subject areas

  • Organic Chemistry

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    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, 74(9), 3370-3377. https://doi.org/10.1021/jo802806z