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学科主题: 生命有机化学
题名: Synthetic Studies toward Galbulimima Alkaloid (-)-GB 13 and (+)-GB 16 and (-)-Himgaline
其他题名: 对galbulimima 生物碱 (-)-GB 13 and (+)-GB 16 and (-)-himgaline的合成研究
作者: Zi WW(资伟伟) ; Yu SY(俞寿云) ; Ma DW(马大为)
通讯作者: 马大为
刊名: Chem.-Asian J.
发表日期: 2011
卷: 6, 期:2, 页:573-579
收录类别: SCI
部门归属: 中科院上海有机化学研究所
英文摘要: Condensation of (S)-3-aminobutan-1-ol with 1,3-cyclohexanedione followed by an intramolecular alkylation afforded bicyclic enamine 32, which was converted into enone 35 through a diastereoselective hydrogenation. Mukaiyama-Michael addition of a bicyclic silyl enol ether to 35 and subsequent stereochemistry inversion by means of an oxidation/reduction strategy provided lactone 41. After reduction of lactone 41 with LAH, Swern oxidation was carried out to give enone 46 upon a spontaneous intramolecular aldol reaction and cleavage of the ketal protecting group. SmI2-mediated carbonyl-alkene reductive coupling of 46 proceeded smoothly in refluxing tetrahydrofuran to deliver pentacyclic intermediate 49, which was oxidized with 2-iodoxybenzoic acid and then treated with trifluoroacetic acid to furnish (-)-GB 13. The overall yield was 6.1% over 19 linear steps. By following the known procedure, our synthetic (-)-GB 13 was converted into himgaline. In addition, by starting from lactone 41, the first total synthesis of (+)-GB 16, a newly isolated member of the gabulimima alkaloid family, was achieved. This synthesis features an intramolecular condensation between an amine and a 1,3-diketone moiety.
语种: 英语
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WOS记录号: WOS:000286440600042
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/15665
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:
Zi WW,Yu SY,Ma DW. Synthetic Studies toward Galbulimima Alkaloid (-)-GB 13 and (+)-GB 16 and (-)-Himgaline[J]. Chem.-Asian J.,2011,6(2):573-579.
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