Synthesis Study on Marmycin A: Preparation of the C3 '-Desmethyl Analogues

doi:10.1021/jo9011078

	Synthesis Study on Marmycin A: Preparation of the C3 '-Desmethyl Analogues
	Ding, Chunyong1,2 ; Tu, Shanghui 2,3; Li, Fuying 2; Wang, Yuanxiang 2; Yao, Qizheng 1; Hu, Wenxiang 3; Xie, Hua4 ; Meng, Linghua4 ; Zhang, Ao2
刊名	JOURNAL OF ORGANIC CHEMISTRY
	2009-08-21
卷号	74 期号:16 页码:6111-6119
ISSN号	0022-3263
DOI	10.1021/jo9011078
文献子类	Article
英文摘要	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.
资助项目	State Key Laboratory of Drug Research[SIMM0809KF-02] ; Chinese National Science Foundation[30772625] ; Shanghai Commission of Science and Technology[07pj14104] ; Chinese Academy of Sciences[00000000]
WOS关键词	NATURALLY-OCCURRING QUINONES ; STEREOSELECTIVE-SYNTHESIS ; ANGUCYCLINONE ANTIBIOTICS ; (+)-RUBIGINONE B-2 ; ARYL AMINES ; GLYCALS ; (+)-OCHROMYCINONE ; (-)-TETRANGOMYCIN ; BENZANNULATION ; TETRANGULOL
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000268907300042
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/279155]
专题	药物化学研究室中科院受体结构与功能重点实验室新药研究国家重点实验室
通讯作者	Yao, Qizheng
作者单位	1.China Pharmaceut Univ, Dept Med Chem, Nanjing 210009, Peoples R China; 2.SIMM, SOMCL, Shanghai 201203, Peoples R China; 3.Capital Normal Univ, Dept Chem, Beijing, Peoples R China; 4.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Div Antitumor Pharmacol, Shanghai 201203, Peoples R China
推荐引用方式 GB/T 7714	Ding, Chunyong,Tu, Shanghui,Li, Fuying,et al. Synthesis Study on Marmycin A: Preparation of the C3 '-Desmethyl Analogues[J]. JOURNAL OF ORGANIC CHEMISTRY,2009,74(16):6111-6119.
APA	Ding, Chunyong.,Tu, Shanghui.,Li, Fuying.,Wang, Yuanxiang.,Yao, Qizheng.,...&Zhang, Ao.(2009).Synthesis Study on Marmycin A: Preparation of the C3 '-Desmethyl Analogues.JOURNAL OF ORGANIC CHEMISTRY,74(16),6111-6119.
MLA	Ding, Chunyong,et al."Synthesis Study on Marmycin A: Preparation of the C3 '-Desmethyl Analogues".JOURNAL OF ORGANIC CHEMISTRY 74.16(2009):6111-6119.