Total Synthesis of Prostaglandin F_<2α> Using Nickel-Catalyzed Stereoselective Cyclization of 1,3-Diene and Tethered Aldehyde via Transmetalation of Nickelacycle with Diisobutylaluminum Acetylacetonate

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概要

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• Total synthesis of prostaglandin F_<2α> utilizing a nickel(0)-catalyzed cyclization of 1,3-diene and tethered aldehyde was achieved. The cyclization proceeded via a transmetalation of nickelacycle with diisobutylaluminum acetylacetonate (^iBu_2-ALAC). Thus, the reaction of 19,having a side chain corresponding to the α-chain in PGF_<2α> with Ni(cod)_2 (10 mol %), PPh_3 (20 mol %), and 1,3-cyclohexadiene (25 mol %) in the presence of ^iBu_2-ALAC (1.5 eq) proceeded stereoselectively to give the cyclized product 26 in 54% yield. During the cyclization of 19,the Z-olefin at C-5 in the side chain completely retained its geometry, and the four contiguous chiral carbon centers in PGF<2α> were stereoselectively constructed. Transformation of the key intermediate 19 into PGF<2α> was successfully achieved.

• 公益社団法人日本薬学会の論文
• 2000-11-01

著者

• 佐藤 美洋

  北海道大学大学院薬学研究院

• Mori Masao

  Faculty Of Hospital Pharmacy Saga Medical School

• 関川 善夫

  Department Of Pharmaceutical Sciences National Institute Of Public Health

• Sato Y

  Osaka Prefecture University

• Sato Y

  (present Address)tsukuba Research Institute Banyu Pharmaceutical Co. Ltd.

• Mori M

  Department Of Pharmacy Saga University Hospital

• Mori M

  Faculty Of Hospital Pharmacy Saga Medical School

• Mori M

  The Institute Of Physical And Chemical Research (riken)

• Sato Y

  Kyoritsu College Of Pharmacy

• 佐藤 嘉信

  Department Of Chemical Engineering University Of Osaka Prefecture

• MORI Miwako

  Graduate School of Pharmaceutical Sciences, Hokkaido University

• SATO Yoshihiro

  Graduate School of Pharmaceutical Sciences, Hokkaido University

• Mori Miwako

  Graduate School Of Pharmaceutical Sciences Hokkaido University

• 森 昌斗

  Hospital Pharmacy Saga Medical School

• TAKIMOTO Masanori

  Graduate School of Pharmaceutical Sciences, Hokkaido University

• Takimoto M

  Graduate School Of Pharmaceutical Sciences Hokkaido University

• Takimoto Masanori

  Graduate School Of Pharmaceutical Sciences Hokkaido University

• Sato Yoshihiro

  Graduate School Of Engineering Osaka City University

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