中性スフィンゴミエリナーゼ阻害剤(+)-スキホスタチンの全合成 [in Japanese] Total Synthesis of (+)-Scyphostatin, a Neutral Sphingomyelinase Inhibitor [in Japanese]
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Scyphostatin, isolated from the culture broth of <I>Trichopeziza mollissima</I> SANK 13892 in 1997, is a powerful and specific inhibitor of neutral sphingomyelinase (N-SMase) and is believed to be a promising new lead for the treatment of AIDS, inflammation, and immunological and neurological disorders. Structurally, this natural product features a novel, highly oxygenated cyclohexane ring incorporated with a C-20 unsaturated fatty acid-substituted amino propanol side chain. In this article, we wish to disclose the whole story of our successful total synthesis of naturally occurring (+) -scyphostatin. In the initial chapter, the first-generation strategy for the enantioselective synthesis of the epoxycyclohexenone part has been described. Subsequently, the second-generation strategy, which led to the first total synthesis of (+) -scyphostatin, has been presented. In the last chapter, the synthesis of several scyphostatin analogues to study the structure-activity relationship has been mentioned briefly.
- J. Synth. Org. Chem. Jpn.
J. Synth. Org. Chem. Jpn. 65(4), 358-369, 2007-04-01
The Society of Synthetic Organic Chemistry, Japan