P-86 紅藻から単離された強力な抗MRSA物質MC7,8の全合成(ポスター発表の部)

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概要

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• Bromomethylthioindoles MC 5-8 are isolated from Laurecia brongniartii as the most potent anti-MRSA substances in red algae. We are interested in the total synthesis of these compounds from the viewpoints of synthetic structural elucidation for the natural products and the structure-activity relationship. Preceding the total synthesis, we developed the introduction methods for 2, 3-disubstituents of the natural products (MC 5-8). The C^3-selective introduction of a methylthio group to unprotected indoles are developed via the C^3-dimethylsulfonium salt of indoles using a DMSO・TFAA complex. The sulfonium salts were easily de-methylated to 3-SMe indoles by refluxing in dipropylamine. It is a new synthetic method for 3-SMe indoles without using stinky thiols in excellent yields. The C^2-selective introduction of dimethylsulfonium or bromo group to 5-NO_2 or 1-Ts 3-SMe indoles are achieved, although 3-SMe indole itself caused dimerization. On the basis of the above findings, we succeeded the first total synthesis of MC 7 and MC 8 as follows. 1) Regio-selective synthesis of C^4-C^6 poly-brominated indoles 21. 2) Introduction of methylthio group into C^3-position of indoles without using stinky thiols. 3) Electrophilic substitution at C^2-position of 3-methylthioindoles 23. The synthesized MC 7, MC 8, and some synthetic intermediates showed potent anti-microbial activities against MRSA. Furthermore, we founded these compounds has potent anti-VRE activities.

• 天然有機化合物討論会の論文
• 2008-09-01

著者

• 亀井 勇統

  佐賀大・海浜セ

• 鈴木 英治

  東邦大・薬

• 濱島 利彦

  東邦大・薬

• 藤田 由紀子

  東邦大・薬

• 森 善昭

  東邦大・薬

• 松原 浩子

  東邦大・薬

• Bekh-Ochir Davaapurev

  東邦大・薬

• 加藤 文男

  東邦大・薬

• 奥野 洋明

  東邦大・薬

関連論文

• 無タンパク培養に適したアワビ消化腺細胞株の樹立 : 動物
• P-86 紅藻から単離された強力な抗MRSA物質MC7,8の全合成(ポスター発表の部)
• 海藻ソゾノハナのジャガイモそうか病防除効果(2007年度大会一般講演要旨)

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