Chem. J. Chinese Universities ›› 2012, Vol. 33 ›› Issue (07): 1476.doi: 10.3969/j.issn.0251-0790.2012.07.020

• Organic Chemistry • Previous Articles     Next Articles

Optimization of Synthetic Method of Marinopyrrole A Derivatives

PAN Li-Li, CHENG Chun-Wei, SONG Hao   

  1. West China School of Pharmacy, Sichuan University, Chengdu 610041, China
  • Received:2011-11-08 Online:2012-07-10 Published:2012-07-10

Abstract: Marinopyrrole A, containing a novel structure with high halogenated bipyrrole, was found to exhibite antibacterrial activity against Methicillin-resistant staphylococcus aureus(MRSA), and against the human cancer cell(HCT-116). Owing to its low potency and high toxicity in vivo, the synthesis of Marinopyrrole A derivatives has become a new hot spot in natural products research.6-Flourobenzene of Marinopyrrole A was obtained by protection, addition step-by-step, oxidation, deprotection of the Ts group, chlorinated and deprotection of methyl group reactions from the starting material dialdehyde compound 1, and finally the yield was 13% after 9-step reactions. The structures of the compounds were confirmed by IR, 1H NMR, 13C NMR and HRMS. Especially, the cyclic ether intermediate 3, necessary in original way, was no longer formed using the addition step-by-step and oxidation, and the total yield was improved. The examination approach provides a new synthetic way for the series Marinopyrrole A derivatives.

Key words: Marinopyrrole A derivative, Cyclic ether intermediate, Optimization of synthesis method

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