Literature DB >> 27215547

Total synthesis, biosynthesis and biological profiles of clavine alkaloids.

Stephanie R McCabe1, Peter Wipf.   

Abstract

This review highlights noteworthy synthetic and biological aspects of the clavine subfamily of ergot alkaloids. Recent biosynthetic insights have laid the groundwork for a better understanding of the diverse biological pathways leading to these indole derivatives. Ergot alkaloids were among the first fungal-derived natural products identified, inspiring pharmaceutical applications in CNS disorders, migraine, infective diseases, and cancer. Pergolide, for example, is a semi-synthetic clavine alkaloid that has been used to treat Parkinson's disease. Synthetic activities have been particularly valuable to facilitate access to rare members of the Clavine family and empower medicinal chemistry research. Improved molecular target identification tools and a better understanding of signaling pathways can now be deployed to further extend the biological and medical utility of Clavine alkaloids.

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Year:  2016        PMID: 27215547      PMCID: PMC4917493          DOI: 10.1039/c6ob00878j

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  51 in total

1.  Enantioselective synthesis of (-)-cis-clavicipitic acid.

Authors:  Jin-Mo Ku; Byeong-Seon Jeong; Sang-sup Jew; Hyeung-geun Park
Journal:  J Org Chem       Date:  2007-09-18       Impact factor: 4.354

2.  Total Synthesis of cis-Clavicipitic Acid from Asparagine via Ir-Catalyzed C-H bond Activation as a Key Step.

Authors:  Yu-ki Tahara; Mamoru Ito; Kyalo Stephen Kanyiva; Takanori Shibata
Journal:  Chemistry       Date:  2015-07-14       Impact factor: 5.236

3.  Two new indole alkaloids, 2-(3,3-dimethylprop-1-ene)-costaclavine and 2-(3,3-dimethylprop-1-ene)-epicostaclavine, from the marine-derived fungus Aspergillus fumigatus.

Authors:  Dahai Zhang; Masayuki Satake; Seketsu Fukuzawa; Kohtaro Sugahara; Ai Niitsu; Tomohiro Shirai; Kazuo Tachibana
Journal:  J Nat Med       Date:  2011-07-27       Impact factor: 2.343

4.  Clavicipitic acid, a new 4-substituted indolic amino acid obtained from submerged cultures of the ergot fungus.

Authors:  J E Robbers; H G Floss
Journal:  Tetrahedron Lett       Date:  1969-05       Impact factor: 2.415

5.  A microwave assisted intramolecular-furan-Diels-Alder approach to 4-substituted indoles.

Authors:  Filip Petronijevic; Cody Timmons; Anthony Cuzzupe; Peter Wipf
Journal:  Chem Commun (Camb)       Date:  2008-11-11       Impact factor: 6.222

6.  Ruthenium-catalyzed cyclocarbonylation of allenyl alcohols and amines: selective synthesis of lactones and lactams.

Authors:  Eiji Yoneda; Shi-Wei Zhang; Da-Yang Zhou; Kiyotaka Onitsuka; Shigetoshi Takahashi
Journal:  J Org Chem       Date:  2003-10-31       Impact factor: 4.354

7.  Formal and total synthesis of (±)-cycloclavine.

Authors:  Nitinkumar D Jabre; Teruki Watanabe; Matthias Brewer
Journal:  Tetrahedron Lett       Date:  2014-01-01       Impact factor: 2.415

8.  A Modular Formal Total Synthesis of (±)-Cycloclavine.

Authors:  Natalie Netz; Till Opatz
Journal:  J Org Chem       Date:  2016-02-04       Impact factor: 4.354

9.  Discovery and reconstitution of the cycloclavine biosynthetic pathway--enzymatic formation of a cyclopropyl group.

Authors:  Dorota Jakubczyk; Lorenzo Caputi; Anaëlle Hatsch; Curt A F Nielsen; Melanie Diefenbacher; Jens Klein; Andrea Molt; Hartwig Schröder; Johnathan Z Cheng; Michael Naesby; Sarah E O'Connor
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-25       Impact factor: 15.336

Review 10.  Diversification of ergot alkaloids in natural and modified fungi.

Authors:  Sarah L Robinson; Daniel G Panaccione
Journal:  Toxins (Basel)       Date:  2015-01-20       Impact factor: 4.546

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  3 in total

Review 1.  Transition Metal-Mediated C-C Single Bond Cleavage: Making the Cut in Total Synthesis.

Authors:  Brian Wang; Melecio A Perea; Richmond Sarpong
Journal:  Angew Chem Int Ed Engl       Date:  2020-08-24       Impact factor: 15.336

2.  Eight-Step Enantioselective Total Synthesis of (-)-Cycloclavine.

Authors:  Stephanie R McCabe; Peter Wipf
Journal:  Angew Chem Int Ed Engl       Date:  2016-11-18       Impact factor: 15.336

3.  Enzyme-Catalyzed Azepinoindole Formation in Clavine Alkaloid Biosynthesis.

Authors:  Kuan-Lin Chen; Chen-Yu Lai; Mai-Truc Pham; Rong-Jie Chein; Yi Tang; Hsiao-Ching Lin
Journal:  Org Lett       Date:  2020-04-03       Impact factor: 6.005

  3 in total

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