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 2010 |
| Externally published | Yes |
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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 journal › Article
}
TY - JOUR
T1 - Total synthesis and cytotoxicity of haterumalides NA and B and their artificial analogues
AU - Hayakawa, Ichiro
AU - Kigoshi, Hideo
PY - 2010/8
Y1 - 2010/8
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
KW - Haterumalides
KW - Marine cytotoxic macrolides
KW - Structure-cytotoxicity relationships
KW - Total synthesis
UR - http://www.scopus.com/inward/record.url?scp=78049367316&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=78049367316&partnerID=8YFLogxK
U2 - 10.5059/yukigoseikyokaishi.68.814
DO - 10.5059/yukigoseikyokaishi.68.814
M3 - Article
AN - SCOPUS:78049367316
VL - 68
SP - 814
EP - 823
JO - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
JF - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
SN - 0037-9980
IS - 8
ER -