P-33 α置換セリン誘導体の不斉合成を基盤とする(+)-ラクタシスチンの不斉全合成研究(ポスター発表の部)

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概要

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• The asymmetric synthesis of α-substituted serine derivatives was accomplished in the following manner. Bislactim ether (11), obtained from prochiral σ-symmetric diethyl aminomalonate (1), was treated with base or Lewis acid in the presence of amine to form the enolate or enaminate (3). Diastereoselective aldol-type reaction of the resultant enolate or enaminate (3) with chiral aldehyde (12) proceeded in a highly stereoselective manner to give the corresponding products (13), respectively. The mediation mode with Sn(II) between 11 and 12 proved to be quite different from that with Mg(II). Reduction of chiral compounds (13) with diisobutylaluminum hydride (DIBAL) followed by hydrolysis with hydrochloric acid afforded the corresponding γ-lactonic α-substituted serines (16). Asymmetric total synthesis of ISP-I (myriocin, thermozymocidin) (6), a potent immunosuppressive compound, has been achieved by utilizing highly diastereoselective aldol reaction of bislactim ether (11) with chiral aldehyde based on the study previously described. We report here a synthetic approach toward (+)-lactacystin (7), the first non-protein neurotropic factor (NTF), based on the asymmetric synthesis of α-substituted serine derivatives as shown in the Scheme 6.

• 天然有機化合物討論会の論文
• 1995-09-01

著者

• 城 始勇

  リガク

• 城 始勇

  理学電機X線研

• 佐野 茂樹

  Graduate School Of Pharmaceutical Sciences The University Of Tokushima

• 佐野 茂樹

  徳島大学薬学部

• 長尾 善光

  Graduate School Of Pharmaceutical Sciences The University Of Tokushima

• 長尾 善光

  徳島大学薬学部

• 佐野 茂樹

  徳島大薬

• 石井 孝拓

  徳島大薬

• 長尾 善光

  徳島大薬

• Nagao Y

  Faculty Of Pharmaceutical Sciences The University Of Tokushima

• Nagao Yoshimitsu

  Faculity Of Pharmaceutical Sciences The University Of Tokushima

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