（±）-百部碱和（±）-三尖杉碱的形式合成。
Formal syntheses of (+/-)-stemonamine and (+/-)-cephalotaxine.
作者信息
Zhao Yu-Ming, Gu Peiming, Zhang Hai-Jun, Zhang Qing-Wei, Fan Chun-An, Tu Yong-Qiang, Zhang Fu-Min
机构信息
State Key Laboratory of Applied Organic Chemistry and Department of Chemistry, Lanzhou University, Lanzhou 730000, PR China.
出版信息
J Org Chem. 2009 Apr 17;74(8):3211-3. doi: 10.1021/jo900113s.
PMID:19320459
Abstract
A short and efficient approach to aza-quaternary pyrrolo[1,2-a]azepine 8 and aza-quaternary indolizine 23, as the crucial intermediates for syntheses of stemonamine (1a) and cephalotaxine (1b), has been developed on the basis of the key intramolecular Schmidt reaction of symmetric azido-diones 5 and 18, respectively.
摘要
基于对称叠氮二酮5和18分别进行的关键分子内施密特反应，已开发出一种简短而有效的方法来合成氮杂季铵化吡咯并[1,2 - a]氮杂卓8和氮杂季铵化中氮茚23，它们是合成百部碱（1a）和三尖杉碱（1b）的关键中间体。
相似文献
1
Formal syntheses of (+/-)-stemonamine and (+/-)-cephalotaxine.（±）-百部碱和（±）-三尖杉碱的形式合成。
J Org Chem. 2009 Apr 17;74(8):3211-3. doi: 10.1021/jo900113s.
2
Synthesis of the tricyclic core in stemonamine alkaloids via one-pot gold(I)-catalyzed cyclization and schmidt rearrangement: formal synthesis of (±)-stemonamine.通过一锅法金（I）催化环化和施密特重排合成百部胺生物碱的三环核心：（±）-百部胺的形式合成
J Org Chem. 2014 Nov 21;79(22):11119-24. doi: 10.1021/jo502103p. Epub 2014 Nov 3.
3
Development of the intramolecular Prins cyclization/Schmidt reaction for the construction of the azaspiro[4,4]nonane: application to the formal synthesis of (±)-stemonamine.发展分子内 Prins 环化/Schmidt 反应构建氮杂螺[4.4]壬烷：在（±）-石蒜碱的形式合成中的应用。
Org Lett. 2011 Feb 18;13(4):724-7. doi: 10.1021/ol102955e. Epub 2011 Jan 13.
4
An efficient total synthesis of (+/-)-stemonamine.（±）-百部碱的高效全合成。
Org Lett. 2008 May 1;10(9):1763-6. doi: 10.1021/ol800433r. Epub 2008 Mar 26.
5
Chiral Brønsted acid-promoted enantioselective desymmetrization in an intramolecular Schmidt reaction of symmetric azido 1,3-hexanediones: asymmetric synthesis of azaquaternary pyrroloazepine skeletons.手性布朗斯特酸促进对称叠氮基1,3 -己二酮分子内施密特反应中的对映选择性去对称化：氮杂季铵化吡咯并氮杂卓骨架的不对称合成。
Chem Asian J. 2011 Jun 6;6(6):1344-7. doi: 10.1002/asia.201100171. Epub 2011 Apr 12.
6
Total synthesis of (±)-maistemonine, (±)-stemonamide, and (±)-isomaistemonine.（±）-马替诺林、（±）-斯蒂莫酰胺和（±）-异马替诺林的全合成。
J Org Chem. 2011 Dec 16;76(24):10173-86. doi: 10.1021/jo202042x. Epub 2011 Nov 23.
7
Azepine synthesis from alkyl azide and propargylic ester via gold catalysis.通过金催化作用，由烷基叠氮化物和炔丙基酯合成氮杂环丙烷。
J Org Chem. 2012 Jun 1;77(11):5184-90. doi: 10.1021/jo300667a. Epub 2012 May 17.
8
Convergency and divergency as strategic elements in total synthesis: the total synthesis of (-)-drupacine and the formal total synthesis of (+/-)-cephalotaxine, (-)-cephalotaxine, and (+)-cephalotaxine.收敛性和发散性作为全合成中的战略要素：（-）-杜巴辛的全合成以及（±）-三尖杉碱、（-）-三尖杉碱和（+）-三尖杉碱的形式全合成
J Org Chem. 2007 Sep 14;72(19):7352-8. doi: 10.1021/jo0710883. Epub 2007 Aug 18.
9
Highly efficient formal synthesis of cephalotaxine, using the Stevens rearrangement--acid lactonization sequence as a key transformation.采用史蒂文斯重排-酸内酯化序列作为关键转化，高效进行了三尖杉宁碱的形式合成。
J Org Chem. 2009 Mar 6;74(5):2213-6. doi: 10.1021/jo8025252.
10
A formal synthesis of (-)-cephalotaxine.（-）-三尖杉碱的形式合成。
Org Lett. 2008 Jul 17;10(14):3045-8. doi: 10.1021/ol8010166. Epub 2008 Jun 13.
引用本文的文献
1
Cytochalasins from Xylaria sp. CFL5, an Endophytic Fungus of Cephalotaxus fortunei.来自三尖杉内生真菌——炭角菌属CFL5的细胞松弛素
Nat Prod Bioprospect. 2021 Feb;11(1):87-98. doi: 10.1007/s13659-020-00279-5. Epub 2020 Nov 4.
2
Cephalotaxus Alkaloids.三尖杉生物碱
Alkaloids Chem Biol. 2017;78:205-352. doi: 10.1016/bs.alkal.2017.07.001. Epub 2017 Aug 16.
3
Overcoming product inhibition in catalysis of the intramolecular Schmidt reaction.克服分子内施密特反应催化中的产物抑制。
J Am Chem Soc. 2013 Jun 19;135(24):9000-9. doi: 10.1021/ja402848c. Epub 2013 Jun 7.
4
Synthesis of medium-bridged twisted lactams via cation-pi control of the regiochemistry of the intramolecular Schmidt reaction.通过阳离子-π 控制分子内施密特反应的区域化学，合成中桥扭曲内酰胺。
J Org Chem. 2010 Feb 19;75(4):1235-43. doi: 10.1021/jo902574m.
Zotero 插件