Literature DB >> 20568766

Total synthesis of (+)-fastigiatine.

Brian B Liau1, Matthew D Shair.   

Abstract

The first total synthesis of the Lycopodium alkaloid (+)-fastigiatine has been accomplished in 15 steps and 30% overall yield from known compounds. Noteworthy transformations include a convergent fragment coupling via a nucleophilic cyclopropane opening, a highly diastereoselective formal [3 + 3]-cycloaddition, and a transannular Mannich reaction to construct the core of the natural product.

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Year:  2010        PMID: 20568766     DOI: 10.1021/ja104575h

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


  8 in total

Review 1.  Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors:  K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal:  Chem Soc Rev       Date:  2012-06-28       Impact factor: 54.564

2.  Alkaloid synthesis: back to basics.

Authors:  Brad M Loertscher; Steven L Castle
Journal:  Nat Chem       Date:  2010-10       Impact factor: 24.427

3.  Total synthesis of the Lycopodium alkaloid serratezomine A using free radical-mediated vinyl amination to prepare a β-stannyl enamine linchpin.

Authors:  Julie A Pigza; Jeong-Seok Han; Aroop Chandra; Daniel Mutnick; Maren Pink; Jeffrey N Johnston
Journal:  J Org Chem       Date:  2012-12-28       Impact factor: 4.354

4.  Stereoselective synthesis of the eastern quinolizidine portion of himeradine A.

Authors:  Nathan D Collett; Rich G Carter
Journal:  Org Lett       Date:  2011-07-12       Impact factor: 6.005

5.  Pyridone annulation via tandem Curtius rearrangement/6π-electrocyclization: total synthesis of (-)-lyconadin C.

Authors:  Xiayun Cheng; Stephen P Waters
Journal:  Org Lett       Date:  2013-08-02       Impact factor: 6.005

6.  Unified total syntheses of fawcettimine class alkaloids: fawcettimine, fawcettidine, lycoflexine, and lycoposerramine B.

Authors:  Guojun Pan; Robert M Williams
Journal:  J Org Chem       Date:  2012-05-07       Impact factor: 4.354

7.  Toward a unified approach for the lycopodines: synthesis of 10-hydroxylycopodine, deacetylpaniculine, and paniculine.

Authors:  Mrinmoy Saha; Rich G Carter
Journal:  Org Lett       Date:  2013-02-05       Impact factor: 6.005

8.  Concise synthesis of (+)-fastigiatine.

Authors:  Renzo A Samame; Christina M Owens; Scott D Rychnovsky
Journal:  Chem Sci       Date:  2015-10-06       Impact factor: 9.825

  8 in total

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