94(P-36) Scyphostainの全合成研究(ポスター発表の部)
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概要
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Scyphostatin was isolated from a mycelial extract of Dasyscyphus mollissimus SANK-13892 in 1997. This is a potent inhibitor of neutral sphingomyelinase. Scyphostatin consists of two segments, the hydrophilic moiety and the hydrophobic moiety. They are characterized by high functionalized cyclohexene ring and a long alkyl chain, respectively. We were interested in both a bioactivity and an unique structure of Scyphostatin. We planned the convergent strategy coupling between the hydrophilic moiety and the hydrophobic moiety of Scyphostatin. We have developed a short and high efficient synthetic route to 4,5-epoxy-2-cyclohexen-1-one derivative, which is the hydrophilic analogue of Scyphostatin. Diels-Alder reaction of a cross-conjugated ketone bearing a spirolactone, obtained from L-Tyrosine by intramolecular lactonization, with cyclopentadiene gave the adduct with high facial selectivity. The adduct was converted to 4,5-epoxy-2-cyclohexen-1-one derivative via epoxidation, 1,2-enone reduction and subsequent epoxidation with high selectivity. For the hydrophobic moiety of Scyphostatin, the stereochemistry of C8 and C10 was introduced by asymmetric acetylation of meso-diol using porcine pancreatic lipase (PPL). The obtained monoacetate was converted to the organozinc compound over several steps. The trisubstituted olefine moiety was constructed by Negishi coupling reaction between a vinyl iodide generated from methyl (S)-hydroxy isobutylate and the organozinc compound.
- 天然有機化合物討論会の論文
- 2002-09-01
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