596792-53-9Relevant academic research and scientific papers
A New Stereoselective Synthesis of Ciguatoxin Right Wing Fragments
Inoue, Masayuki,Yamashita, Shuji,Tatami, Atsushi,Miyazaki, Keisuke,Hirama, Masahiro
, p. 2797 - 2804 (2007/10/03)
The right wings (13 and 14) of ciguatoxins were synthesized highly stereoselectively. Key transformations in the synthesis are (i) an oxiranyl anion strategy to attach the H ring, (ii) intramolecular carbonyl olefination to cyclize the J ring, (iii) regio- and stereoselective reduction of the epoxyacetal to install the C42-stereocenter, and (iv) stereoselective reductive etherification to construct the K ring. The present procedure greatly improved the stereoselectivity and efficiency in comparison to a previous synthesis. Remarkably, only 23 steps were required from monocyclic I ring 5 to construct the ciguatoxin right wings. The high practicality of the present synthesis ensures a sufficient supply of these complex fragments for total syntheses and biomedical applications.
A concise route to the right wing of ciguatoxin
Tatami, Atsushi,Inoue, Masayuki,Uehara, Hisatoshi,Hirama, Masahiro
, p. 5229 - 5233 (2007/10/03)
A concise route to the HIJKLM-ring fragment 10 of ciguatoxin (CTX) and 51-hydroxyCTX3C was developed in which oxiranyl anion addition and intramolecular carbonyl olefination were utilized as key transformations. The present procedure requires only 23 steps from the I-ring 5, while 35 steps were employed in a previous synthesis of the corresponding right wing 11 of CTX3C. The high efficiency of the present synthesis ensures a supply of 10 for total synthesis and biomedical applications.
