60 サフラマイシンBの全合成研究

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概要

• 論文の詳細を見る

• Saframycins are antitumor antibiotics, produced by Streptomyces lavendulae. We now report a total synthesis of saframycin B. The high functionalized piperazine-2, 5-diones (18a-d), which were prepared from the corresponding aldehyde (10) in 7 steps, were reduced by Li(t-BuO)_3AlH to give the unstable allylic alcohols (19). When heated in formic acid, 19 was converted to the desired hexahydro-1, 5-imino-3-benzazocine derivatives (20). (R=i-Pr, 52% yield). Compound (20d) was converted into the pentacyclic compound (33b) in 12 steps. Oxidation of 33b with 10N HNO_3 afforded 2 in 1% yield. The yield of 2 was raised to 41% by a two step sequence (i, BBr_3, -78℃, ii, 10N HNO_3). The synthetic saframycin B was identical with the natural saframycin B in spectral (MS, UV, IR (CHCl_3). ^1H-NMR, ^<13>C-NMR) properties.

• 天然有機化合物討論会の論文
• 1986-09-09

著者

• 齋藤 直樹

  Meiji Pharmaceutical University

• 齋藤 直樹

  明治薬大薬

• 久保 陽徳

  明治薬大薬

• 久保 陽徳

  明治薬科大学

• 大和 秀一

  Meiji College of Pharmacy

• 大和 秀一

  明治薬大

• 中村 まどか

  明治薬大

• Kubo Akinori

  Graduate School Of Pharmaceutical Sciences Meiji Pharmaceutical University

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