Convergent synthesis of the E'FGH' ring fragment of ciguatoxin 1B via an acetylene cobalt complex strategy.
[reaction: see text] A convergent synthesis of the E'FGH' ring fragment of ciguatoxin has been accomplished through (i) coupling between the E' ring-acetylide and the H' ring-aldehyde, (ii) stereoselective F ring cyclization via an acetylene cobalt complex, (iii) conversion to a carbonyl function, and (iv) reductive hydroxy-ketone cyclization to construct the G ring.
Takai
Shigeyuki
S
Laboratory of Organic Chemistry, Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan.
Isobe
Minoru
M
D000114:Acetylene / Q000737:chemistry*; D002922:Ciguatoxins; D003035:Cobalt / Q000737:chemistry*; D007202:Indicators and Reagents; D008387:Marine Toxins / Q000138:chemical synthesis*; D008958:Models, Molecular; D008968:Molecular Conformation; D001618:beta-Lactamases / Q000138:chemical synthesis*
D007202:Indicators and Reagents; D008387:Marine Toxins; C454647:ciguatoxin 1B (CTX 1B); D002922:Ciguatoxins; D003035:Cobalt; D001618:beta-Lactamases; D000114:Acetylene