Literature DB >> 26716762

Total Synthesis of Gelsenicine via a Catalyzed Cycloisomerization Strategy.

Eric T Newcomb1, Phil C Knutson1, Blaine A Pedersen1, Eric M Ferreira1.   

Abstract

The first total synthesis of (±)-gelsenicine is reported. The synthetic route is highly efficient (13 steps), featuring (1) a pivotal metal-catalyzed isomerization/rearrangement process that forges the central core of the molecule and (2) two facile C-N bond-forming steps that establish the flanking heterocycles.

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Year:  2015        PMID: 26716762      PMCID: PMC4732274          DOI: 10.1021/jacs.5b12263

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  32 in total

1.  Total synthesis of (+)-fawcettidine.

Authors:  Jennifer A Kozak; Gregory R Dake
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  First total synthesis of ent-gelsedine via a novel iodide-promoted allene N-acyliminium ion cyclization.

Authors:  W G Beyersbergen van Henegouwen; R M Fieseler; F P Rutjes; H Hiemstra
Journal:  J Org Chem       Date:  2000-12-01       Impact factor: 4.354

3.  Koumine, Humantenine, and Yohimbane Alkaloids from Gelsemium elegans.

Authors:  You-Kai Xu; Lin Yang; Shang-Gao Liao; Pei Cao; Bin Wu; Hua-Bin Hu; Juan Guo; Ping Zhang
Journal:  J Nat Prod       Date:  2015-06-23       Impact factor: 4.050

4.  Enantioselective total synthesis of (-)-citrinadin A and revision of its stereochemical structure.

Authors:  Zhiguo Bian; Christopher C Marvin; Stephen F Martin
Journal:  J Am Chem Soc       Date:  2013-07-18       Impact factor: 15.419

5.  An enantioselective total synthesis and stereochemical revision of (+)-citrinadin B.

Authors:  Ke Kong; John A Enquist; Monica E McCallum; Genessa M Smith; Takanori Matsumaru; Elnaz Menhaji-Klotz; John L Wood
Journal:  J Am Chem Soc       Date:  2013-07-18       Impact factor: 15.419

6.  Total Synthesis of (+)-Gelsedine.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  1999-08       Impact factor: 15.336

7.  Total Synthesis of Gelsemoxonine through a Spirocyclopropane Isoxazolidine Ring Contraction.

Authors:  Stefan Diethelm; Erick M Carreira
Journal:  J Am Chem Soc       Date:  2015-05-04       Impact factor: 15.419

8.  Biomimetic total synthesis of (+)-gelsemine.

Authors:  Xuan Zhou; Tao Xiao; Yusuke Iwama; Yong Qin
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-04       Impact factor: 15.336

9.  Total synthesis of bryostatin 16 using atom-economical and chemoselective approaches.

Authors:  Barry M Trost; Guangbin Dong
Journal:  Nature       Date:  2008-11-27       Impact factor: 49.962

10.  Total synthesis of (+)-gelsemine via an organocatalytic Diels-Alder approach.

Authors:  Xiaoming Chen; Shengguo Duan; Cheng Tao; Hongbin Zhai; Fayang G Qiu
Journal:  Nat Commun       Date:  2015-05-21       Impact factor: 14.919

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  5 in total

1.  C-C Bond Migration in the Cycloisomerization of 1,6-Enynes.

Authors:  Susan M Stevenson; Eric T Newcomb; Eric M Ferreira
Journal:  Org Chem Front       Date:  2016-06-30       Impact factor: 5.281

2.  Chirality Transfer and Asymmetric Catalysis: Two Strategies toward the Enantioselective Formal Total Synthesis of (+)-Gelsenicine.

Authors:  Phil C Knutson; Haofan Ji; Christopher M Harrington; Yan-Ting Ke; Eric M Ferreira
Journal:  Org Lett       Date:  2022-07-07       Impact factor: 6.072

3.  Synthesis of 1,3-Diynes via Cadiot-Chodkiewicz Coupling of Volatile, in Situ Generated Bromoalkynes.

Authors:  Phil C Knutson; Haleigh E Fredericks; Eric M Ferreira
Journal:  Org Lett       Date:  2018-10-17       Impact factor: 6.005

Review 4.  Metal-mediated synthesis of pyrrolines.

Authors:  Noelia S Medran; Agustina La-Venia; Sebastian A Testero
Journal:  RSC Adv       Date:  2019-02-27       Impact factor: 4.036

5.  Iron-Catalyzed Cycloisomerization and C-C Bond Activation to Access Non-canonical Tricyclic Cyclobutanes.

Authors:  Frederik Kramm; Franziska Ullwer; Benedict Klinnert; Min Zheng; Bernd Plietker
Journal:  Angew Chem Int Ed Engl       Date:  2022-08-08       Impact factor: 16.823

  5 in total

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