Literature DB >> 18254631

A direct route to fluostatin C by a fascinating Diels-Alder reaction.

Maolin Yu1, Samuel J Danishefsky.   

Abstract

The Diels-Alder reactions between vinylindenes (5 or 6) as the dienes with quinoneketals (7 or 8) or with methacrolein as the dienophiles were investigated. The remarkable regioselectivities of these Diels-Alder adducts suggested that the regiopreferences of these dienes and dienophiles in these cases are not a fixed property of each component of the cycloaddition but are mutually contigent. This paper shows how the Diels-Alder reaction between 6 and 8 was applied to the inaugural total syntheses of fluostatin C and E.

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Year:  2008        PMID： 18254631     DOI： 10.1021/ja7113757

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


  8 in total

1.  Synthesis of o-chlorophenols via an unexpected nucleophilic chlorination of quinone monoketals mediated by N,N'-dimethylhydrazine dihydrochloride.

Authors:  Zhiwei Yin; Jinzhu Zhang; Jing Wu; Riana Green; Sihan Li; Shengping Zheng
Journal:  Org Biomol Chem       Date:  2014-05-14       Impact factor: 3.876

2.  Practical radical cyclizations with arylboronic acids and trifluoroborates.

Authors:  Jonathan W Lockner; Darryl D Dixon; Rune Risgaard; Phil S Baran
Journal:  Org Lett       Date:  2011-09-16       Impact factor: 6.005

3.  Fluostatins produced by the heterologous expression of a TAR reassembled environmental DNA derived type II PKS gene cluster.

Authors:  Zhiyang Feng; Jeff H Kim; Sean F Brady
Journal:  J Am Chem Soc       Date:  2010-09-01       Impact factor: 15.419

4.  Synthesis and chemical diversity analysis of bicyclo[3.3.1]non-3-en-2-ones.

Authors:  Jared T Hammill; Julia Contreras-García; Aaron M Virshup; David Beratan; Weitao Yang; Peter Wipf
Journal:  Tetrahedron       Date:  2010-03-31       Impact factor: 2.457

5.  Enantioselective (formal) aza-Diels-Alder reactions with non-Danishefsky-type dienes.

Authors:  Uttam K Tambar; Sharon K Lee; James L Leighton
Journal:  J Am Chem Soc       Date:  2010-08-04       Impact factor: 15.419

6.  Cationic-oxazaborolidine-catalyzed enantioselective Diels-Alder reaction of alpha,beta-unsaturated acetylenic ketones.

Authors:  Joshua N Payette; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

7.  Palladium-catalyzed enantioselective addition of two distinct nucleophiles across alkenes capable of quinone methide formation.

Authors:  Katrina H Jensen; Tejas P Pathak; Yang Zhang; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2009-12-02       Impact factor: 15.419

8.  Synthetic Studies of the Rubellin Natural Products: Development of a Stereoselective Strategy and Total Synthesis of (+)-Rubellin C.

Authors:  Jackson A Gartman; Uttam K Tambar
Journal:  J Org Chem       Date:  2021-07-21       Impact factor: 4.198
  8 in total

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