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学科主题: 生命有机化学
题名: Total Synthesis of Candicanoside A, a Rearranged Cholestane Disaccharide, and Its 4 ''-O-(p-Methoxybenzoate) Congener
其他题名: 一个重排甾体二糖苷Candicanoside A及4''-O-对甲氧基苯甲酰基同系物的合成
作者: Tang PP(汤平平) ; Yu B(俞飚)
通讯作者: 俞飚
刊名: Eur. J. Org. Chem.
发表日期: 2009
期: 2, 页:259-269
收录类别: SCI
部门归属: 上海有机所
英文摘要: Candicanoside A (1) and its 4 ''-O-(p-methoxybenzoate) derivative 2 are congeners of the novel 24(23 -> 22)abeo-cholestane glycosides that occur in the genus Ornithogalum indigenous to Southern Africa and have remarkable cytostatic activities. These two saponins have been synthesized starting from dehydroisoandrosterone, D-glucose, and L-rhamnose in 37 and 44 steps, respectively. The reaction protocols feature a stereocontrolled stepwise glycosylation with glycosyl imidates as the donors. The synthesis of the rearranged steroid aglycon employs a 20-alkoxy radical-mediated functionalization of the angular 1.8-methyl group, a Johnson-Claisen rearrangement for the alkylation at C-20, an aldol condensation at C-22, and a photodeconjugation of an alpha,beta-unsaturated lactone as the key steps. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000262897700009
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/19105
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:
Tang PP,Yu B. Total Synthesis of Candicanoside A, a Rearranged Cholestane Disaccharide, and Its 4 ''-O-(p-Methoxybenzoate) Congener[J]. Eur. J. Org. Chem.,2009(2):259-269.
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