440320-44-5Relevant academic research and scientific papers
Convergent synthesis of the ABCDE ring system of ciguatoxin CTX3C
Maruyama, Megumi,Inoue, Masayuki,Oishi, Tohru,Oguri, Hiroki,Ogasawara, Yoshihiro,Shindo, Yumi,Hirama, Masahiro
, p. 1835 - 1851 (2002)
Ciguatoxin CTX3C is a representative congener of the ciguatoxins, which are known to be the principal causative-agents of ciguatera seafood poisoning. The structure of CTX3C spans over three nanometers and is characterized by thirteen ether rings. To attain a practical construction of this molecule, efficient supplies of the structural fragments are crucial. Herein we report the convergent synthesis of the ABCDE ring fragment featuring (i) alkylative coupling of the AB ring and E ring, and (ii) ring-closing olefin metathesis.
A concise route to two distinct E-ring structures of ciguatoxins
Inoue, Masayuki,Iwatsu, Masafumi,Yamashita, Shuji,Hirama, Masahiro
, p. 327 - 338 (2008/03/12)
Ciguatoxins, the causative toxins of ciguatera seafood poisoning, are large ladder-like polycyclic ethers, and known to have more than 20 structurally distinct congeners. In this paper, we describe a new concise synthesis of the two E-ring structures, of
Highly stereocontrolled synthesis of the ABCD ring fragment of ciguatoxin CTX3C
Oishi,Tanaka,Ogasawara,Maeda,Oguri,Hirama
, p. 952 - 954 (2007/10/03)
A combination of asymmetric alkylation using (1R,2S)-1-amino-2-indanol derivative as a chiral auxiliary and the ring-closing metathesis reaction was shown to be an efficient method for synthesizing the ABCD ring fragment of ciguatoxin CTX3C.
