P-66 抗腫瘍活性を有する(+)および(-)ペリコシンAの全合成と絶対立体構造の決定(ポスター発表の部)

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概要

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• The isolation of antitumor natural products pericosines A-E as metabolites of Periconia byssoides OUPS-N133 originally separated from the sea hare. Aplysia kurodai. was reported in 1997-2000, and their structures are shown. However, the absolute configuration of pericosine A had not been elucidated despite its significant antitumor activity. Our successful symmetric total synthesis of the reported structure of pericosine A led us to conclude that the structure was incorrect. Here, we report the total synthesis of (+)-and (-)-pericosine A and the structure revision and determination of the absolute configuration of the antitumor natural product pericosine A in full detail. The cyclohexene derivative 9 has been transformed from (-)-shikimic acid followed by oxidation with O_sO_4 to give a diol as a single product. The key reaction in this total synthesis of chloride atom introduction was achieved by the addition of excess of SOCl_2 to 5 to afford chlorinated product 19 in 42°_o yield. The structure of key intermediate 19 was confirmed by detailed 1D and 2D NMR studies. As the results. the structure of 19 was disclosed that the chloride atom was not introduced via S_Ni mechanism as we had aimed early on. but via S_N mechanism with syn selectivity. To complete the total synthesis, 19 was deprotected with TFA to give the final product (4'). Finally. the total synthesis of natural pericosine A (4) was achieved via antipode alcohol 16' from (-)-quinic acid.

• 天然有機化合物討論会の論文
• 2007-08-24

著者

• Usami Yoshiko

  Clinical Research Center Nagoya National Hospital:tokai Area Central Hospital For Aids Treatment And

• 宇佐美 吉英

  大阪薬大

• 大杉 茉梨恵

  大阪薬大

• 市川 隼人

  大阪薬大

• 有本 正生

  大阪薬大

• 高岡 伊三夫

  大阪薬大

• 堀部 祐介

  大阪薬大

• 富山 俊輔

  大阪薬大

• 大塚 三紗子

  大阪薬大

• 今西 由美

  大阪薬大

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