Total Synthesis of Estrone via Estriol Dimethyl Ether

  • 朝子 典彦
    Chemical Research Laboratories, Central Research Division, Takeda Chemical Industries, Ltd.
  • 平賀 謙太郎
    Chemical Research Laboratories, Central Research Division, Takeda Chemical Industries, Ltd.
  • 三木 卓一
    Chemical Research Laboratories, Central Research Division, Takeda Chemical Industries, Ltd.

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説明

Meerwein-Ponndorf reduction of 3-methoxy-8,14-secoestra-1,3,5 (10), 9,15-pentaene-14,17-dione (III) yielded a mixture of rac-17α- and 17β-hydroxy-3-methoxy-8,14-secoestra-1,3,5 (10), 9,15-pentaen-14-one (XI and XII). Cyclization of 17β-benzoate of XII gave 3,16α-dimethoxy estra-1,3,5 (10), 8,14-pentaen-17β-ol 17-benzoate (XV), which was further transformed to rac-estrone (XXI).

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