Literature DB >> 26097263

Construction of the 5,6,7-tricyclic skeleton of lancifodilactone F.

Heping Shi1, Saptarshi De1, Qiaoling Wang1, Shuanhu Gao1, Xiao Wang1, Chuo Chen1.   

Abstract

We report herein the synthesis of a fully functionalized B,C,D-ring system of lancifodilactone F. The key transformations involve an arene-olefin meta-photocycloaddition reaction and a palladium-catalyzed oxidative C-C cleavage reaction to establish its B,C-rings.

Entities:  

Keywords:  cycloaddition; oxidation; palladium; photochemistry; terpenoid

Year:  2015        PMID： 26097263      PMCID： PMC4472376          DOI： 10.1016/j.tetlet.2014.12.054

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  17 in total

1.  Collective domino approach toward the core of molecules isolated from the genus Schisandra.

Authors:  Alexandra Bartoli; Gaëlle Chouraqui; Jean-Luc Parrain
Journal:  Org Lett       Date:  2011-12-01       Impact factor: 6.005

2.  Photochemistry of arenes--reloaded.

Authors:  Jochen Mattay
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  Photochemical reactions as key steps in organic synthesis.

Authors:  Norbert Hoffmann
Journal:  Chem Rev       Date:  2008-02-27       Impact factor: 60.622

4.  Diastereoselective total synthesis of (±)-schindilactone A.

Authors:  Qing Xiao; Wei-Wu Ren; Zhi-Xing Chen; Tian-Wen Sun; Yong Li; Qin-Da Ye; Jian-Xian Gong; Fan-Ke Meng; Lin You; Yi-Fan Liu; Ming-Zhe Zhao; Ling-Min Xu; Zhen-Hua Shan; Ying Shi; Ye-Feng Tang; Jia-Hua Chen; Zhen Yang
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-07       Impact factor: 15.336

5.  Enantioselective synthesis of the predominant AB ring system of the Schisandra nortriterpenoid natural products.

Authors:  Birgit Gockel; Shermin S Goh; Emma J Puttock; Hannah Baars; Guilhem Chaubet; Edward A Anderson
Journal:  Org Lett       Date:  2014-08-15       Impact factor: 6.005

6.  Lancifodilactone F: a novel nortriterpenoid possessing a unique skeleton from Schisandra lancifolia and its anti-HIV activity.

Authors:  Wei-Lie Xiao; Rong-Tao Li; Sheng-Hong Li; Xiao-Li Li; Han-Dong Sun; Yong-Tang Zheng; Rui-Rui Wang; Yang Lu; Cheng Wang; Qi-Tai Zheng
Journal:  Org Lett       Date:  2005-03-31       Impact factor: 6.005

7.  Diastereoselective total synthesis of (±)-schindilactone a, Part 3: The final phase and completion.

Authors:  Wei-Wu Ren; Zhi-Xing Chen; Qing Xiao; Yong Li; Tian-Wen Sun; Zi-Yang Zhang; Qin-Da Ye; Fan-Ke Meng; Lin You; Ming-Zhe Zhao; Ling-Min Xu; Ye-Feng Tang; Jia-Hua Chen; Zhen Yang
Journal:  Chem Asian J       Date:  2012-07-03

8.  Diastereoselective total synthesis of (±)-schindilactone A, Part 1: Construction of the ABC and FGH ring systems and initial attempts to construct the CDEF ring system.

Authors:  Tian-Wen Sun; Wei-Wu Ren; Qing Xiao; Ye-Feng Tang; Yan-Dong Zhang; Yong Li; Fan-Ke Meng; Yi-Fan Liu; Ming-Zhe Zhao; Ling-Min Xu; Jia-Hua Chen; Zhen Yang
Journal:  Chem Asian J       Date:  2012-07-03

Review 9.  Triterpenoids from the Schisandraceae family.

Authors:  Wei-Lie Xiao; Rong-Tao Li; Sheng-Xiong Huang; Jian-Xin Pu; Han-Dong Sun
Journal:  Nat Prod Rep       Date:  2008-07-31       Impact factor: 13.423

10.  The arene-alkene photocycloaddition.

Authors:  Ursula Streit; Christian G Bochet
Journal:  Beilstein J Org Chem       Date:  2011-04-28       Impact factor: 2.883
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  4 in total

1.  Photoassisted Synthesis of Complex Molecular Architectures: Dearomatization of Benzenoid Arenes with Aza-o-xylylenes via an Unprecedented [2+4] Reaction Topology.

Authors:  Dmitry M Kuznetsov; Olga A Mukhina; Andrei G Kutateladze
Journal:  Angew Chem Int Ed Engl       Date:  2016-04-21       Impact factor: 15.336

Review 2.  Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models.

Authors:  Nicole D Bartolo; Jacquelyne A Read; Elizabeth M Valentín; K A Woerpel
Journal:  Chem Rev       Date:  2020-01-06       Impact factor: 60.622

3.  Total Synthesis of (+)-Rubriflordilactone A.

Authors:  Shermin S Goh; Guilhem Chaubet; Birgit Gockel; Marie-Caroline A Cordonnier; Hannah Baars; Andrew W Phillips; Edward A Anderson
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-04       Impact factor: 15.336

4.  Total Synthesis of the Schisandraceae Nortriterpenoid Rubriflordilactone A.

Authors:  Guilhem Chaubet; Shermin S Goh; Mujahid Mohammad; Birgit Gockel; Marie-Caroline A Cordonnier; Hannah Baars; Andrew W Phillips; Edward A Anderson
Journal:  Chemistry       Date:  2017-09-08       Impact factor: 5.236
  4 in total

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