Literature DB >> 21818165

Benzothiazines in organic synthesis. An approach to floresolide B.

Yugang Chen1, Michael Harmata.   

Abstract

The intramolecular conjugate addition of a sulfoximine carbanion to an α,β-unsaturated ester results in the formation of a benzothiaine bearing a benzylic stereocenter with extremely high fidelity. We have used this methodology to complete a formal total synthesis of the antitumor agent (+)-floresolide B.

Entities:  

Year:  2011        PMID： 21818165      PMCID： PMC3147297          DOI： 10.1016/j.tetlet.2011.05.091

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  9 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 synthesis. A total synthesis of pseudopteroxazole.

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

3.  Total synthesis of floresolide B and Delta(6,7)-Z-floresolide B.

Authors:  K C Nicolaou; Hao Xu
Journal:  Chem Commun (Camb)       Date:  2006-01-20       Impact factor: 6.222

4.  The intramolecular, stereoselective addition of sulfoximine carbanions to alpha,beta-unsaturated esters.

Authors:  Michael Harmata; Xuechuan Hong
Journal:  J Am Chem Soc       Date:  2003-05-14       Impact factor: 15.419

5.  Benzothiazines in synthesis. Further studies of the intramolecular, stereoselective addition of sulfonimidoyl carbanions to alpha,beta-unsaturated functional groups.

Authors:  Michael Harmata; Kanok-on Rayanil; Vinson R Espejo; Charles L Barnes
Journal:  J Org Chem       Date:  2009-04-17       Impact factor: 4.354

6.  Benzothiazines in synthesis. A formal total synthesis of pseudopteroxazole.

Authors:  Michael Harmata; Zhengxin Cai; Yugang Chen
Journal:  J Org Chem       Date:  2009-08-07       Impact factor: 4.354

7.  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

8.  Benzothiazines in synthesis: studies directed toward the synthesis of erogorgiaene.

Authors:  Michael Harmata; Xuechuan Hong; Peter R Schreiner
Journal:  J Org Chem       Date:  2008-01-24       Impact factor: 4.354

9.  Benzothiazines in organic synthesis. The preparation of enantiomerically pure 4-substituted quinolones.

Authors:  Michael Harmata; Xuechuan Hong
Journal:  Org Lett       Date:  2007-06-08       Impact factor: 6.005
  9 in total
  2 in total

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

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

Review 2.  Quinone and hydroquinone metabolites from the ascidians of the genus Aplidium.

Authors:  Camila Spereta Bertanha; Ana Helena Januário; Tavane Aparecida Alvarenga; Letícia Pereira Pimenta; Márcio Luis Andrade E Silva; Wilson Roberto Cunha; Patrícia Mendonça Pauletti
Journal:  Mar Drugs       Date:  2014-06-12       Impact factor: 5.118
  2 in total

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