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

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  • Total Synthesis of (+)-Scyphostatin, a Neutral Sphingomyelinase Inhibitor
  • チュウセイ スフィンゴミエリナーゼ ソガイザイ スキホスタチン ノ ゼンゴウセイ

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Scyphostatin, isolated from the culture broth of Trichopeziza mollissima 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.

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