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Literature DB >> 21958431

Total synthesis of (±)-dragmacidin E.

Abstract

The bis indole sponge alkaloid dragmacidin E was synthesized in racemic form over 25 steps starting from 7-benzhydroxyindole. Key steps include (a) a Witkop cyclization to facilitate construction of the indole-spanning seven-membered ring and (b) a cyclodehydrative pyrazinone synthesis that unites the two indole-containing sectors.

Entities: Chemical Disease Gene

Mesh：

Substances：

Year: 2011 PMID： 21958431 PMCID： PMC3200574 DOI： 10.1021/ol202535f

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

13 in total

1. The total synthesis of (+)-dragmacidin F.

Authors: Neil K Garg; Daniel D Caspi; Brian M Stoltz
Journal: J Am Chem Soc Date: 2004-08-11 Impact factor: 15.419

2. Concise photochemical synthesis of the antimalarial indole alkaloid decursivine.

Authors: Mark Mascal; Kyle V Modes; Asuman Durmus
Journal: Angew Chem Int Ed Engl Date: 2011-04-07 Impact factor: 15.336

3. Total synthesis of (±)-decursivine and (±)-serotobenine: a Witkop photocyclization/elimination/O-Michael addition cascade approach.

Authors: Hua Qin; Zhengren Xu; Yuxin Cui; Yanxing Jia
Journal: Angew Chem Int Ed Engl Date: 2011-04-18 Impact factor: 15.336

4. Dragmacidins: new protein phosphatase inhibitors from a southern australian deep-water marine sponge, spongosorites sp

Authors:
Journal: J Nat Prod Date: 1998-05 Impact factor: 4.050

5. The first total synthesis of dragmacidin d.

Authors: Neil K Garg; Richmond Sarpong; Brian M Stoltz
Journal: J Am Chem Soc Date: 2002-11-06 Impact factor: 15.419

6. Development of an enantiodivergent strategy for the total synthesis of (+)- and (-)-dragmacidin f from a single enantiomer of quinic Acid.

Authors: Neil K Garg; Daniel D Caspi; Brian M Stoltz
Journal: J Am Chem Soc Date: 2005-04-27 Impact factor: 15.419

7. Dragmacidin E synthesis studies. Preparation of a model cycloheptannelated indole fragment.

Authors: Ken S Feldman; Paiboon Ngernmeesri
Journal: Org Lett Date: 2005-11-24 Impact factor: 6.005

Review 8. A unified synthetic approach to the pyrazinone dragmacidins.

Authors: Neil K Garg; Brian M Stoltz
Journal: Chem Commun (Camb) Date: 2006-07-18 Impact factor: 6.222

9. Dragmacidin E synthesis studies. Preparation of a model heptacyclic core structure.

Authors: Ken S Feldman; Paiboon Ngernmeesri
Journal: Org Lett Date: 2010-10-15 Impact factor: 6.005

10. Total synthesis of marine sponge bis(indole) alkaloids of the topsentin class.

Authors: Xavier Guinchard; Yannick Vallée; Jean-Noël Denis
Journal: J Org Chem Date: 2007-04-20 Impact factor: 4.354

5 in total

1. Syntheses of Cyclic Guanidine-Containing Natural Products.

Authors: Yuyong Ma; Saptarshi De; Chuo Chen
Journal: Tetrahedron Date: 2015-02-25 Impact factor: 2.457

2. Total Synthesis of (±)-Dragmacidin E: Problems Solved and Lessons Learned.

Authors: Ken S Feldman; Paiboon Ngernmeesri
Journal: Synlett Date: 2012-08 Impact factor: 2.454

3. Asymmetric hydrovinylation of vinylindoles. A facile route to cyclopenta[g]indole natural products (+)-cis-trikentrin A and (+)-cis-trikentrin B.

Authors: Wang Liu; Hwan Jung Lim; T V RajanBabu
Journal: J Am Chem Soc Date: 2012-03-13 Impact factor: 15.419

4. TFA-mediated synthesis of functionalized pyrano[2,3-c]pyrazoles from pyrazol-3-ones, active carbonyl compounds and tert-BuOH.

Authors: Issa Yavari; Jamil Sheykhahmadi
Journal: Mol Divers Date: 2021-03-02 Impact factor: 2.943

5. Palladium-Catalyzed Aminocyclization-Coupling Cascades: Preparation of Dehydrotryptophan Derivatives and Computational Study.

Authors: Belén Vaz; Claudio Martínez; Francisco Cruz; J Gabriel Denis; Ángel R de Lera; José M Aurrecoechea; Rosana Álvarez
Journal: J Org Chem Date: 2021-06-14 Impact factor: 4.354

5 in total