Literature DB >> 19537725

Benzothiazines in synthesis. A formal total synthesis of pseudopteroxazole.

Michael Harmata1, Zhengxin Cai, Yugang Chen.   

Abstract

A formal total synthesis of the antitubercular natural product was accomplished. This work was undertaken to address certain stereochemical problems in our initial synthesis. By using an ester group as a surrogate for a methyl group, we were able to intercept a key intermediate in our first synthesis with better selectivity and greater convergence than had previously been the case.

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Year:  2009        PMID: 19537725      PMCID: PMC2821684          DOI: 10.1021/jo9009112

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


  12 in total

Review 1.  Natural product growth inhibitors of Mycobacterium tuberculosis.

Authors:  Brent R Copp; A Norrie Pearce
Journal:  Nat Prod Rep       Date:  2006-11-28       Impact factor: 13.423

Review 2.  Natural products, small molecules, and genetics in tuberculosis drug development.

Authors:  Maria-Teresa Gutierrez-Lugo; Carole A Bewley
Journal:  J Med Chem       Date:  2008-04-05       Impact factor: 7.446

3.  A One-Pot, One-Operation

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  1999-08       Impact factor: 15.336

4.  Novel antimycobacterial benzoxazole alkaloids, from the west Indian Sea whip Pseudopterogorgia elisabethae.

Authors:  A D Rodríguez; C Ramírez; I I Rodríguez; E González
Journal:  Org Lett       Date:  1999-08-12       Impact factor: 6.005

5.  Benzothiazines in synthesis. A total synthesis of pseudopteroxazole.

Authors:  Michael Harmata; Xuechuan Hong
Journal:  Org Lett       Date:  2005-08-04       Impact factor: 6.005

6.  Total synthesis of marinomycins A-C and of their monomeric counterparts monomarinomycin A and iso-monomarinomycin A.

Authors:  K C Nicolaou; Andrea L Nold; Robert R Milburn; Corinna S Schindler; Kevin P Cole; Junichiro Yamaguchi
Journal:  J Am Chem Soc       Date:  2007-01-24       Impact factor: 15.419

7.  Enantiospecific synthesis of the proposed structure of the antitubercular marine diterpenoid pseudopteroxazole: revision of stereochemistry.

Authors:  T W Johnson; E J Corey
Journal:  J Am Chem Soc       Date:  2001-05-16       Impact factor: 15.419

8.  Palladium-catalyzed N-arylation of sulfoximines with aryl bromides and aryl iodides

Authors: 
Journal:  J Org Chem       Date:  2000-01-14       Impact factor: 4.354

Review 9.  Tuberculosis: a search for novel therapy starting with natural products.

Authors:  L A Mitscher; W Baker
Journal:  Med Res Rev       Date:  1998-11       Impact factor: 12.944

10.  Benzothiazines in synthesis. Toward the synthesis of pseudopteroxazole.

Authors:  Michael Harmata; Xuechuan Hong; Charles L Barnes
Journal:  Org Lett       Date:  2004-06-24       Impact factor: 6.005

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  5 in total

1.  Oxidation of 4-methoxyanilines to 1,4-benzoquinones using ceric ammonium nitrate (CAN).

Authors:  Yugang Chen; Weijiang Ying; Michael Harmata
Journal:  Tetrahedron Lett       Date:  2011-01-26       Impact factor: 2.415

2.  Benzothiazines in organic synthesis. An approach to floresolide B.

Authors:  Yugang Chen; Michael Harmata
Journal:  Tetrahedron Lett       Date:  2011-08-10       Impact factor: 2.415

3.  Toward the total synthesis of elisapterosin B: A Hg(OTf)(2)-promoted diastereoselective intramolecular Friedel-Crafts alkylation reaction.

Authors:  Weijiang Ying; Charles L Barnes; Michael Harmata
Journal:  Tetrahedron Lett       Date:  2011-01-12       Impact factor: 2.415

4.  Preparation of S-2-halophenyl-2,1-benzothiazines.

Authors:  Aswin Garimalla; Michael Harmata
Journal:  Tetrahedron       Date:  2021-02-10       Impact factor: 2.457

5.  Evaluation of pseudopteroxazole and pseudopterosin derivatives against Mycobacterium tuberculosis and other pathogens.

Authors:  Malcolm W B McCulloch; Brad Haltli; Douglas H Marchbank; Russell G Kerr
Journal:  Mar Drugs       Date:  2012-08-15       Impact factor: 6.085

  5 in total

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