Synthesis Study on Marmycin A: Preparation of the C3′-Desmethyl Analogues
Synthesis Study on Marmycin A: Preparation of the C3′-Desmethyl Analogues
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DOI：
10.1021/jo9011078
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发表时间：
2009-08-21
影响因子：
3.6
通讯作者：
Zhang, Ao
中科院分区：
文献类型：
--
作者：
Ding, Chunyong;Tu, Shanghui;Zhang, Ao
对天然产物marmycin A的全合成进行了研究。以脱羧烷基化、Pd(OAc)(2)催化环化、芳构化和C-N偶联为关键步骤，建立了关键片段8-氨基-3-甲基苯并[a]蒽酮(1)的快速合成策略。然而，由于未能获得碳水化合物片段 2，marmycin A 的最终组装受到阻碍。相反，通过使用 InBr3 催化的 C 和 N-糖苷化反应，以中等产率制备了 marmycin A 去甲基类似物的小型文库。这些化合物的绝对构型通过将它们的光谱数据与报告的marmycin A.的光谱数据进行比较并通过X射线分析来证实。
Total synthesis of natural product marmycin A was studied. An expeditious synthetic strategy for the key fragment 8-amino-3-methylbenz[a]anthraduinone (1) was established with decarboxylative alkylation, Pd(OAc)(2)-catalyzed cyclization, aromatization, and C-N coupling as the key steps. However, final assembly of marmycin A was hampered by the failure to obtain the carbohydrate fragment 2. Instead, a small library of desmethyl analogues of marmycin A was prepared in moderate yields by using the InBr3-catalyzed C- and N-glycosidation reaction. The absolute configuration of these compounds was confirmed by comparison of their spectroscopic data with that reported for marmycin A. and by X-ray analysis.