Literature DB >> 15469270

Enantioselective total synthesis of (+)-gigantecin: exploiting the asymmetric glycolate aldol reaction.

Michael T Crimmins1, Jin She.   

Abstract

The enantioselective synthesis of the potent, selective, cytotoxic, annonaceous acetogenin, (+)-gigantecin, has been completed. An asymmetric glycolate aldol serves to establish the stereocenters at C13,14 and at C21,22. A Carreira asymmetric acetylide addition is used to establish the C17 stereocenter.

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Year:  2004        PMID: 15469270     DOI: 10.1021/ja0455852

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


  7 in total

1.  Synthesis of (+)-bullatacin via the highly diastereoselective [3+2] annulation reaction of a racemic aldehyde and a nonracemic allylsilane.

Authors:  Jennifer M Tinsley; Eric Mertz; Pek Y Chong; Robert-André F Rarig; William R Roush
Journal:  Org Lett       Date:  2005-09-15       Impact factor: 6.005

2.  Total synthesis of (-)-mucocin.

Authors:  Michael T Crimmins; Yan Zhang; Frank A Diaz
Journal:  Org Lett       Date:  2006-05-25       Impact factor: 6.005

3.  Highly stereoselective and scalable anti-aldol reactions using N-(p-dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide: scope and origins of stereoselectivities.

Authors:  Hua Yang; Subham Mahapatra; Paul Ha-Yeon Cheong; Rich G Carter
Journal:  J Org Chem       Date:  2010-11-05       Impact factor: 4.354

4.  Total Synthesis of Amphidinolide E and Amphidinolide E Stereoisomers.

Authors:  Porino Va; William R Roush
Journal:  Tetrahedron       Date:  2007-06-25       Impact factor: 2.457

5.  Asymmetric total synthesis of pyranicin.

Authors:  Michael T Crimmins; Danielle L Jacobs
Journal:  Org Lett       Date:  2009-06-18       Impact factor: 6.005

6.  Total synthesis of annonaceous acetogenins belonging to the non-adjacent bis-THF and non-adjacent THF-THP sub-classes.

Authors:  Ian B Spurr; Richard C D Brown
Journal:  Molecules       Date:  2010-01-21       Impact factor: 4.411

7.  Recent progress on the total synthesis of acetogenins from Annonaceae.

Authors:  Nianguang Li; Zhihao Shi; Yuping Tang; Jianwei Chen; Xiang Li
Journal:  Beilstein J Org Chem       Date:  2008-12-05       Impact factor: 2.883

  7 in total

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