Studies toward the total synthesis of scyphostatin: first entry to the highly functionalized cyclohexenone segment.
The cyclohexenone segment 2 of scyphostatin (1), a potent inhibitor of neutral sphingomyelinase, was synthesized in an enantioselective manner starting from the bromo ether 5 and D-serinal derivative 3. The synthetic method features a coupling reaction of 5 with 3 to construct the asymmetric quaternary carbon center and a stereospecific epoxide ring formation as the key steps.
Izuhara
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Sagami Chemical Research Center, Nishi-Ohnuma, Sagamihara, Kanagawa 229-0012, Japan.
Katoh
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D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D003512:Cyclohexanones / Q000138:chemical synthesis; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013108:Sphingomyelin Phosphodiesterase / Q000037:antagonists & inhibitors*; D013237:Stereoisomerism
D000577:Amides; D003512:Cyclohexanones; D004791:Enzyme Inhibitors; D007202:Indicators and Reagents; D011753:Pyrones; C121123:scyphostatin; D013108:Sphingomyelin Phosphodiesterase