以双醛化合物1为原料,通过取代基保护、分步加成、氧化、脱Ts(对甲苯磺酰基)、氯代和脱甲基等反应,以9步反应13%的总收率合成了苯环6位含氟取代的Marinopyrrole A衍生物12,所合成化合物的结构经IR,1H NMR,13C NMR和HRMS分析确证.分步加成和氧化的应用有效避免了原合成方法中环醚中间体3的生成,提高了反应总收率,为系列Marinopyrrole A衍生物的合成提供了一种新方法.
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.