Synthesis Study on Marmycin A: Preparation of the C3′-Desmethyl Analogues
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- 作者：Chunyong Ding ; Shanghui Tu ; Fuying Li ; Yuanxiang Wang ; Qizheng Yao ; Wenxiang Hu ; Hua Xie ; Linghua Meng ; Ao Zhang
- 刊名：Journal of Organic Chemistry
- 出版年：2009
- 出版时间：August 21, 2009
- 年：2009
- 卷：74
- 期：16
- 页码：6111-6119
- 全文大小：969K
- 年卷期：v.74,no.16(August 21, 2009)
- ISSN：1520-6904
文摘
Total synthesis of natural product marmycin A was studied. An expeditious synthetic strategy for the key fragment 8-amino-3-methylbenz[a]anthraquinone (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.