Studies toward the total synthesis of scyphostatin: first entry to the highly functionalized cyclohexenone segment |
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Authors: | Izuhara T Katoh T |
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Affiliation: | Sagami Chemical Research Center, Nishi-Ohnuma, Sagamihara, Kanagawa 229-0012, Japan. |
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Abstract: | 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. |
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