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 | |
| 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
Fingerprint Dive into the research topics of 'Total synthesis and cytotoxicity of haterumalides NA and B and their artificial analogues'. Together they form a unique fingerprint.
Cite this
Hayakawa, I., & Kigoshi, H. (2010). Total synthesis and cytotoxicity of haterumalides NA and B and their artificial analogues. Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 68(8), 814-823. https://doi.org/10.5059/yukigoseikyokaishi.68.814