Suppr超能文献

通过二乙烯基吡咯啉的电环化闭环反应全合成(±)-γ-石蒜烷。

Total synthesis of (±)-γ-lycorane via the electrocyclic ring closure of a divinylpyrroline.

作者信息

Huntley Raymond J, Funk Raymond L

机构信息

Department of Chemistry, Pennsylvania State University, University Park, Pennsylvaia, 16802, USA.

出版信息

Tetrahedron Lett. 2011 Dec 14;52(50):6671-6674. doi: 10.1016/j.tetlet.2011.09.138.

Abstract

A concise total synthesis of (±)-γ-lycorane is described. The key step in the synthesis is the 6π-electrocyclic ring closure of a divinylpyrroline to give a tetrahydroindole, which is subsequently hydrogenated to give the all-cis indolizidine core.

摘要

本文描述了(±)-γ-石蒜碱的简洁全合成方法。该合成的关键步骤是二乙烯基吡咯啉的6π-电环化闭环反应生成四氢吲哚,随后将其氢化得到全顺式中氮茚核心。

相似文献

1
Total synthesis of (±)-γ-lycorane via the electrocyclic ring closure of a divinylpyrroline.
Tetrahedron Lett. 2011 Dec 14;52(50):6671-6674. doi: 10.1016/j.tetlet.2011.09.138.
6
Efficient synthesis of cyclic amidine-based fluorophores 6π-electrocyclic ring closure.
Chem Sci. 2020 Mar 13;11(14):3586-3591. doi: 10.1039/d0sc00798f.
8
Stereoselective 6π-electron electrocyclic ring closures of 2-halo-amidotrienes via a remote 1,6-asymmetric induction.
Org Lett. 2010 Dec 17;12(24):5768-71. doi: 10.1021/ol102693e. Epub 2010 Nov 19.
9
Synthesis of indoles via 6pi-electrocyclic ring closures of trienecarbamates.
J Am Chem Soc. 2006 Apr 19;128(15):4946-7. doi: 10.1021/ja060282o.

引用本文的文献

1
Synthetic Approaches to α-, β-, γ-, and δ-lycoranes.
European J Org Chem. 2023 Sep 14;26(35). doi: 10.1002/ejoc.202300404. Epub 2023 Jul 11.
2
Applications of Friedel-Crafts reactions in total synthesis of natural products.
RSC Adv. 2018 Dec 3;8(70):40061-40163. doi: 10.1039/c8ra07325b. eCollection 2018 Nov 28.
3
The Pictet-Spengler Reaction Updates Its Habits.
Molecules. 2020 Jan 19;25(2):414. doi: 10.3390/molecules25020414.

本文引用的文献

1
Mild oxidation of tosylmethylisocyanide to tosylmethylisocyanate: utility in synthetic and medicinal chemistry.
Tetrahedron Lett. 2014 Mar 19;55(12):2003-2005. doi: 10.1016/j.tetlet.2014.02.016.
2
A chiral 1,2-bisphospholane ligand with a novel structural motif: applications in highly enantioselective Rh-catalyzed hydrogenations.
Angew Chem Int Ed Engl. 2002 May 3;41(9):1612-4. doi: 10.1002/1521-3773(20020503)41:9<1612::aid-anie1612>3.0.co;2-h.
4
An approach to the total synthesis of welwistatin.
Org Lett. 2006 Jun 8;8(12):2643-5. doi: 10.1021/ol0608799.
5
Synthesis of indoles via 6pi-electrocyclic ring closures of trienecarbamates.
J Am Chem Soc. 2006 Apr 19;128(15):4946-7. doi: 10.1021/ja060282o.
10
Amaryllidaceae and Sceletium alkaloids.
Nat Prod Rep. 1994 Jun;11(3):329-32. doi: 10.1039/np9941100329.

文献AI研究员

20分钟写一篇综述,助力文献阅读效率提升50倍。

立即体验

用中文搜PubMed

大模型驱动的PubMed中文搜索引擎

马上搜索

文档翻译

学术文献翻译模型,支持多种主流文档格式。

立即体验