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题名: Total Syntheses of the Tetracyclic Cyclopiane Diterpenes Conidiogenone, Conidiogenol, and ConidiogenoneB
其他题名: Total Syntheses of the Tetracyclic Cyclopiane Diterpenes Conidiogenone, Conidiogenol, and Conidiogenone B
作者: Hou, SH; Tu, YQ(涂永强); Wang, SH(王少华); Xi, CC; Zhang, FM(张辅民); Wang, SH(王少华); Li, YT; Liu, L
收录类别: SCIE ; EI ; MEDLINE
出版日期: 2016-03-24
刊名: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷号: 55, 期号:14, 页码:4456-4460
英文摘要: Total syntheses of the biologically important and structurally unique tetracyclic diterpenes conidiogenone, conidiogenol, and conidiogenoneB of the cyclopiane class are reported. The absolute configuration of naturally occurring conidiogenoneB was also corrected. The key step of our strategy involved the highly efficient construction of both ringC and the quaternary carbon center shared by rings A and C through a one-step regioselective and diastereoselective cycloenlargement in the form of a semipinacol-type rearrangement. In particular, the desired regioselectivity was made possible by properly adjusting the migratory aptitude of the migrating carbon atom through the introduction of an electron-donating phenylthio group at this position.
关键词: cyclization ; natural products ; semipinacol rearrangement ; tetracyclic diterpenes ; total synthesis
作者部门: [Hou, Si-Hua ; Tu, Yong-Qiang ; Wang, Shuang-Hu ; Xi, Chao-Chao ; Zhang, Fu-Min ; Wang, Shao-Hua ; Liu, Lin] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China ; [Hou, Si-Hua ; Tu, Yong-Qiang ; Wang, Shuang-Hu ; Xi, Chao-Chao ; Zhang, Fu-Min ; Wang, Shao-Hua ; Liu, Lin] Lanzhou Univ, Coll Chem & Chem Engn, Lanzhou 730000, Peoples R China ; [Tu, Yong-Qiang ; Li, Yan-Tao] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China ; [Tu, Yong-Qiang] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300072, Peoples R China
通讯作者: Tu, YQ (reprint author), Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China. ; Tu, YQ (reprint author), Lanzhou Univ, Coll Chem & Chem Engn, Lanzhou 730000, Peoples R China. ; Tu, YQ (reprint author), Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China. ; Tu, YQ (reprint author), Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300072, Peoples R China.
学科分类: Chemistry
文章类型: Article
所属项目编号: NSFC [21202073, 21290180, 21272097, 21372104, 21472077] ; MOE ; MOST [2012ZX 09201101-003]
所属项目名称: 国家自然科学基金项目 ; 国家科技重大专项
项目资助者: NSFC ; MOST ; MOE
语种: 英语
DOI: 10.1002/anie.201600529
ISSN号: 1433-7851
WOS记录号: WOS:000373133000005
EI记录号: 20161002074849
PM记录号: 26937844
IR记录号: WOS:000373133000005
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内容类型: 期刊论文
URI标识: http://ir.lzu.edu.cn/handle/262010/180387
Appears in Collections:化学化工学院_期刊论文

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Recommended Citation:
Hou, SH,Tu, YQ,Wang, SH,et al. Total Syntheses of the Tetracyclic Cyclopiane Diterpenes Conidiogenone, Conidiogenol, and ConidiogenoneB[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2016,55(14):4456-4460.
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