P-25 海綿由来37員環マクロリドTheonezolide A〜Cの立体化学の解明(ポスター発表の部)

概要

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Theonezolides A〜C isolated from the Okinawan marine sponge Theonella sp. are unique 37-membered macrolides have various functionalities such as a sulfate ester, an oxazole, a thiazole group, three 1,3-diols and two 1,3,5-triols. They have potent cytotoxic activity in vitro and caused a marked platelet shape change at low concentrations. Theonezolides A〜C have 23 chiral centers which of five were determined by synthetic means, whereas 18 chiral centers remain undefined. The stereochemistry of 18 chiral centers in theonezolides A〜C was mainly elucidated by detailed analysis of ROESY data and coupling constants. J(H,H) values were obtained by the resolution-enhanced ^1H NMR spectra and decoupling experiments. On the other hands, J(C,H) values were measured by HETLOC, J-resolved-HSQC, phase-sensitive HMBC, and J-impeach-HMBC spectra. To determine C-57/C59 relationship, we planed synthesis of two diastereomers of model compounds for C-55-C-63 portion, and it is in progress.
天然有機化合物討論会の論文
2006-09-15