Total Synthesis of Mimosamycin

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概要

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• The synthesis of mimosamycin has been achieved in 6 steps starting from 7-hydroxy-6-methylisoquinoline (7). Copper-catalyzed autoxidation of 7,which was prepared in 80% over-all yield in 5 steps from 3-methoxy-4-methylbenzaldehyde, gave 6-methyl-3,5-dimorpholino-7,8-dioxo-7,8-dihydroisoquinoline (8a). Upon treatment with sulfuric acid-methanol followed by diazomethane, the o-quinone (8a) was converted to 7-methoxy-6-methyl-3-morpholino-5,8-dioxo-5,8-dihydroisoquinoline (10a). Reductive acetylation of 10a with zinc-acetic acid and acetic anhydride gave 5,8-diacetoxy-7-methoxy-6-methyl-3-morpholinoisoquinoline, which was quaternized at the isoquinoline nitrogen with methyl iodide. Treatment of the methiodide (12a) with silver oxide gave rise to in one-step 7-methoxy-2,6-dimethyl-3,5,8-trioxo-2,3,5,8-tetrahydroisoquinoline, which was identified with a specimen of natural mimosamycin isolated from the culture filtrate of Streptomyces lavendulae No. 314.

• 公益社団法人日本薬学会の論文
• 1978-07-25

著者

• 福見 宏

  Medicinal Chemistry Research Laboratories, Sankyo Co., Ltd.,

• 三島 洋

  Central Research Laboratories, Sankyo Co., Ltd.

• 福見 宏

  Medicinal Chemistry Research Laboratories Sankyo Co. Ltd.

• 三島 洋

  Central Research Laboratories Sankyo Co. Ltd.

• 栗原 英志

  Central Research Laboratories Sankyo Co. Ltd.

• 栗原 英志

  三共(株)活性物質研究所

• 福見 宏

  Central Research Laboratories, Sankyo Co., Ltd.

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