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学科主题: 天然产物有机化学
题名: An Enantioselective Convergent Route to Pamamycin 621A
其他题名: Pamamycin 621A的一种汇聚式合成
作者: Ren GB(任国宝) ; Huang YX(黄祎先) ; Sun YP(孙亚平) ; Li ZH(李中晗) ; Wu YK(伍贻康)
通讯作者: 伍贻康
刊名: J. Org. Chem.
发表日期: 2010
卷: 75, 期:15, 页:5048-5064
收录类别: SCI
部门归属: 中国科学院上海有机化学研究所
英文摘要: An effective approach to the total synthesis of natural antibiotic pamamycin 621A is described, in which the stereogenic centers at the C-13 and C-15 were taken from a chiral building block derived from the inexpensive D-glucolactone while all others (except the C-10) were installed via chiral auxiliary-induced asymmetric Evans/Crimmins aldol reactions. In the synthesis of the smaller/lower fragment, an antiselective Evans aldol condensation was found to occur only if a stoichiometric (rather than catalytic as reported in the literature) amount of magnesium chloride was present. A previously unknown effect of the steric bulkiness of the pyridine base employed on the stereochemical outcome of the formation of the THF ring in the presence of a chiral auxiliary was also observed. The THF rings in the larger/upper fragment were similarly synthesized with a high level of stereoselectivity from a linear precursor carrying a chiral auxiliary via intramolecular O-alkylations, most notably even under acidic conditions. The basic dimethylamino functionality at the C-15 was installed at the final stage of the whole synthesis, with those otherwise unavoidable side reactions in the conversion of the azido group effectively circumvented through using a very mild yet largely forgotten tributyltin reduction protocol.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000280398100018
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/20447
Appears in Collections:生命有机化学国家重点实验室_期刊论文

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Recommended Citation:
Ren GB,Huang YX,Sun YP,et al. An Enantioselective Convergent Route to Pamamycin 621A[J]. J. Org. Chem.,2010,75(15):5048-5064.
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