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学科主题: 天然产物有机化学
题名: A chiron approach to the total synthesis of (+)-aculeatin D
其他题名: 基于手性元法的(+)-Aculeatin D的全合成
作者: Gao J(高剑) ; Zhen ZB(甄志彬) ; Wu YK(伍贻康)
通讯作者: 伍贻康
刊名: J. Org. Chem.
发表日期: 2008
卷: 73, 期:18, 页:7310-7316
收录类别: SCI
部门归属: 中国科学院上海有机所
英文摘要: A synthesis of natural aculeatin D has been achieved, with the key stereogenic centers taken from inexpensive and readily available D-xylose. In elaboration Of D-Xylose into a desired form readily applicable in synthesis a previously misinterpreted and overlooked abnormal selectivity in hydroxyl protection was noticed and exploited. Protocols were developed for monotosylation of a triol insoluble in CH2Cl2, and "freezing" the less stable isomer (aculeatin D) at the PIFA-mediated oxidative spirocyclization, respectively. An unexplained deprotonation at a benzyl protecting group by a thermodynamically more stable dithiane carbanion in the literature was also addressed.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000259195200046
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/20409
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:
Gao J,Zhen ZB,Wu YK. A chiron approach to the total synthesis of (+)-aculeatin D[J]. J. Org. Chem.,2008,73(18):7310-7316.
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