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

Ichiro Hayakawa, Hideo Kigoshi

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)814-823
Number of pages10
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume68
Issue number8
DOIs
Publication statusPublished - Aug 2010
Externally publishedYes

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Cytotoxicity
Macrolides
Stereochemistry
Esters
Animals
Cells

Keywords

  • Biselides
  • Haterumalides
  • Marine cytotoxic macrolides
  • Structure-cytotoxicity relationships
  • Total synthesis

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Total synthesis and cytotoxicity of haterumalides NA and B and their artificial analogues. / Hayakawa, Ichiro; Kigoshi, Hideo.

In: Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, Vol. 68, No. 8, 08.2010, p. 814-823.

Research output: Contribution to journalArticle

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