Literature DB >> 18855482

A versatile synthesis of unsymmetrical 3,3'-bioxindoles: stereoselective Mukaiyama aldol reactions of 2-siloxyindoles with isatins.

J Michael Ellis1, Larry E Overman, Huw R Tanner, Jocelyn Wang.   

Abstract

A new synthesis of 3,3'-bioxindoles is reported that is well suited for the preparation of unsymmetrical structures. In the key step, 3-hydroxy-3,3'-bioxindoles are constructed by Mukaiyama aldol reaction of 2-siloxyindoles with isatins. These tertiary carbinols are formed in high diastereoselectivities, with substitution at various positions of the isatin and the 2-siloxyindole being tolerated.

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Year:  2008        PMID： 18855482      PMCID： PMC2634855          DOI： 10.1021/jo801867w

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  11 in total

1.  Diastereoselection in lewis-Acid-mediated aldol additions.

Authors:  R Mahrwald
Journal:  Chem Rev       Date:  1999-05-12       Impact factor: 60.622

2.  Investigation of a dialkylation approach for enantioselective construction of vicinal quaternary stereocenters.

Authors:  S B Hoyt; L E Overman
Journal:  Org Lett       Date:  2000-10-05       Impact factor: 6.005

3.  Enantioselective total synthesis of the cyclotryptamine alkaloid idiospermuline.

Authors:  Larry E Overman; Emily A Peterson
Journal:  Angew Chem Int Ed Engl       Date:  2003-06-06       Impact factor: 15.336

4.  Chemistry and biology of diazonamide A: second total synthesis and biological investigations.

Authors:  K C Nicolaou; Junliang Hao; Mali V Reddy; Paraselli Bheema Rao; Gerasimos Rassias; Scott A Snyder; Xianhai Huang; David Y-K Chen; William E Brenzovich; Nicolas Giuseppone; Aurora O'Brate; Paraskevi Giannakakou
Journal:  J Am Chem Soc       Date:  2004-10-13       Impact factor: 15.419

5.  Palladium-catalyzed enantioselective cyclization of silyloxy-1,6-enynes.

Authors:  Britton K Corkey; F Dean Toste
Journal:  J Am Chem Soc       Date:  2007-02-17       Impact factor: 15.419

6.  Enantioselective total synthesis of (+)-gliocladin C.

Authors:  Larry E Overman; Youseung Shin
Journal:  Org Lett       Date:  2007-01-18       Impact factor: 6.005

7.  Organocatalytic asymmetric direct alpha-alkynylation of cyclic beta-ketoesters.

Authors:  Thomas B Poulsen; Luca Bernardi; José Aleman; Jacob Overgaard; Karl Anker Jørgensen
Journal:  J Am Chem Soc       Date:  2007-01-17       Impact factor: 15.419

8.  Asymmetric construction of quaternary carbon stereocenters: high stereoselection in Mukaiyama aldol reactions of 2-siloxyindoles with chiral aldehydes.

Authors:  Susanta Adhikari; Sebastien Caille; Martin Hanbauer; Vinh X Ngo; Larry E Overman
Journal:  Org Lett       Date:  2005-06-23       Impact factor: 6.005

9.  Palladium asymmetric allylic alkylation of prochiral nucleophiles: horsfiline.

Authors:  Barry M Trost; Megan K Brennan
Journal:  Org Lett       Date:  2006-05-11       Impact factor: 6.005

10.  Total synthesis of complex cyclotryptamine alkaloids: stereocontrolled construction of quaternary carbon stereocenters.

Authors:  Alan Steven; Larry E Overman
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336
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  2 in total

1.  Synthesis of the bicyclic welwitindolinone core via an alkylation/cyclization cascade reaction.

Authors:  John A Brailsford; Ryan Lauchli; Kenneth J Shea
Journal:  Org Lett       Date:  2009-11-19       Impact factor: 6.005

Review 2.  Studies on the alkaloids of the calycanthaceae and their syntheses.

Authors:  Jin-Biao Xu; Ke-Jun Cheng
Journal:  Molecules       Date:  2015-04-15       Impact factor: 4.411
  2 in total

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