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

被引：31

作者：

Ding, Chunyong ^{[1
,2
]}

Tu, Shanghui ^{[2
,3
]}

Li, Fuying ^{[2
]}

Wang, Yuanxiang ^{[2
]}

Yao, Qizheng ^{[1
]}

Hu, Wenxiang ^{[3
]}

Xie, Hua ^{[4
]}

Meng, Linghua ^{[4
]}

Zhang, Ao ^{[2
]}

机构：

[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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 16期

基金：

美国国家科学基金会;

关键词：

NATURALLY-OCCURRING QUINONES; STEREOSELECTIVE-SYNTHESIS; ANGUCYCLINE ANTIBIOTICS; GLYCALS; (+)-OCHROMYCINONE; (-)-TETRANGOMYCIN; BENZANNULATION; CONVENIENT;

D O I：

10.1021/jo9011078

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

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.

引用

页码：6111 / 6119

页数：9

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