抄録
Maitotoxin (MTX) is a ladder-shaped polyether produced by an epiphytic dinoflagellate. As a part of our structure-activity relationship studies using synthetic partial structures of MTX, the QRS ring comprising a 6/6/7 tricyclic system was synthesized through stereoselective construction of five contiguous stereogenic centers on the Q ring via i) coupling of a Weinreb amide and a furyllithium, followed by ii) Noyori asymmetric transfer hydrogenation, iii) the Achmatowicz reaction, iv) chemoselective methylation of a methyl acetal in the presence of a carbonyl group by treatment with Me2Zn/BF3·OEt2, v) highly diastereoselective dihydroxylation, and vi) ring expansion of a six-membered to a seven-membered ring ketone. The synthetic specimen inhibited MTX-induced Ca2+influx with an IC50 value of 44 μM.
本文言語 | English |
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ページ(範囲) | 1904-1906 |
ページ数 | 3 |
ジャーナル | Chemistry Letters |
巻 | 43 |
号 | 12 |
DOI | |
出版ステータス | Published - 2014 |
ASJC Scopus subject areas
- 化学 (全般)