Mirror Image Synthesis of Left Ends of Ciguatoxin and Gambiertoxin 4b.
Three compounds related to the AB fragments of ciguatoxin and gambiertoxin 4b and two diastereomers (at the C-2 position) of the ABC fragment of ciguatoxin have been synthesized in enantiomeric form. The stereochemistry of the C-2 position was introduced selectively from the corresponding pentose derivative. Construction of the A ring with its side chain was completed by Nicholas type cyclization of an acetylene bis(cobalthexacarbonyl) complex followed by reductive decomplexation.
Hosokawa
Seijiro
S
Laboratory of Organic Chemistry, School of Bioagricultural Sciences, Nagoya University Chikusa, Nagoya 464-8601, Japan.
Isobe
Minoru
M