Literature DB >> 24511164

Formal and total synthesis of (±)-cycloclavine.

Nitinkumar D Jabre1, Teruki Watanabe1, Matthias Brewer1.   

Abstract

A ring fragmentation and intramolecular azomethine ylide 1,3-dipolar cycloaddition sequence of reactions was successfully used in the preparation of a known (±)-cycloclavine precursor in good overall yield. Results of efforts to incorporate the tetrasubstituted cyclopropane ring present in cycloclavine are also discussed.

Entities:  

Keywords:  1,3-Dipolar Cycloaddition; Cycloclavine; Ergot Alkaloid; Natural Product Synthesis; Ring Fragmentation

Year:  2014        PMID： 24511164      PMCID： PMC3915717          DOI： 10.1016/j.tetlet.2013.10.152

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


  16 in total

1.  Total synthesis of (±)-cycloclavine and (±)-5-epi-cycloclavine.

Authors:  Filip R Petronijevic; Peter Wipf
Journal:  J Am Chem Soc       Date:  2011-04-28       Impact factor: 15.419

2.  Lewis acid promoted carbon-carbon bond cleavage of gamma-silyloxy-beta-hydroxy-alpha-diazoesters.

Authors:  Cristian Draghici; Matthias Brewer
Journal:  J Am Chem Soc       Date:  2008-03-06       Impact factor: 15.419

3.  [Cycloclavin, a new alkaloid from Ipomoea hildebrandtii Vatke. 71. Ergot alkaloids].

Authors:  D Stauffacher; P Niklaus; H Tscherter; H P Weber; A Hofmann
Journal:  Tetrahedron       Date:  1969-12       Impact factor: 2.457

4.  Diastereoselective zinco-cyclopropanation of chiral allylic alcohols with gem-dizinc carbenoids.

Authors:  Jean-François Fournier; Simon Mathieu; André B Charette
Journal:  J Am Chem Soc       Date:  2005-09-28       Impact factor: 15.419

5.  Synthesis of demissidine by a ring fragmentation 1,3-dipolar cycloaddition approach.

Authors:  Zhe Zhang; Geoffrey M Giampa; Cristian Draghici; Qiufeng Huang; Matthias Brewer
Journal:  Org Lett       Date:  2013-04-15       Impact factor: 6.005

6.  Deconstructing cytisine: The syntheses of (+/-)-cyfusine and (+/-)-cyclopropylcyfusine, fused ring analogs of cytisine.

Authors:  Daniel Yohannes; Kristen Procko; Lorraine A Lebel; Carol B Fox; Brian T O'Neill
Journal:  Bioorg Med Chem Lett       Date:  2008-03-06       Impact factor: 2.823

7.  Tandem cyclopropanation with dibromomethane under Grignard conditions.

Authors:  Gerhard Brunner; Laura Eberhard; Jürg Oetiker; Fridtjof Schröder
Journal:  J Org Chem       Date:  2008-09-11       Impact factor: 4.354

8.  Preparation of a storable zinc carbenoid species and its application in cyclopropanation, chain extension, and [2,3]-sigmatropic rearrangement reactions.

Authors:  Arnaud Voituriez; Lucie E Zimmer; André B Charette
Journal:  J Org Chem       Date:  2010-02-19       Impact factor: 4.354

9.  An efficient synthetic approach to polycyclic 2,5-dihydropyrroles from alpha-silyloxy ketones.

Authors:  Cristian Draghici; Qiufeng Huang; Matthias Brewer
Journal:  J Org Chem       Date:  2009-11-06       Impact factor: 4.354

10.  Stereospecific cyclopropanation of highly substituted C-C double bonds promoted by CrCl2. Stereoselective synthesis of cyclopropanecarboxamides and cyclopropyl ketones.

Authors:  José M Concellón; Humberto Rodríguez-Solla; Carmen Méjica; Elena G Blanco
Journal:  Org Lett       Date:  2007-07-13       Impact factor: 6.005
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  4 in total

1.  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

Review 2.  Total synthesis, biosynthesis and biological profiles of clavine alkaloids.

Authors:  Stephanie R McCabe; Peter Wipf
Journal:  Org Biomol Chem       Date:  2016-05-24       Impact factor: 3.876

3.  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 Weinheim Bergstr Ger       Date:  2015-02-25

4.  A Route to the C,D,E Ring System of the Aspidosperma Alkaloids.

Authors:  Geoffrey M Giampa; Jian Fang; Matthias Brewer
Journal:  Org Lett       Date:  2016-08-08       Impact factor: 6.005
  4 in total

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