Literature DB >> 15646992

Total synthesis of (+/-)-mycothiazole and formal enantioselective approach.

Alexandre Le Flohic1, Christophe Meyer, Janine Cossy.   

Abstract

[Reaction: see text] A total synthesis of (+/-)-mycothiazole and a formal enantioselective approach have been achieved from 2,4-dibromothiazole. A chain extension of a homoallylic alcohol proceeding through an unsaturated sultone intermediate, generated by ring-closing metathesis, was used as a key step for the elaboration of the conjugated (Z)-dienol moiety.

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Year:  2005        PMID： 15646992     DOI： 10.1021/ol047603q

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  7 in total

1.  A Catalytic Approach for Enantioselective Synthesis of Homoallylic Alcohols Bearing a Z-Alkenyl Chloride or Trifluoromethyl Group. A Concise and Protecting Group-Free Synthesis of Mycothiazole.

Authors:  Ryan J Morrison; Farid W van der Mei; Filippo Romiti; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2019-12-24       Impact factor: 15.419

2.  Reinvestigation of Mycothiazole Reveals the Penta-2,4-dien-1-ol Residue Imparts Picomolar Potency and 8S Configuration.

Authors:  Tyler A Johnson; Joseph D Morris; David A Coppage; Colon V Cook; Lauren N Persi; Marcos A Ogarrio; Taylor C Garcia; Nicole L McIntosh; Erin P McCauley; Joseph Media; Mani Maheshwari; Frederick A Valeriote; Jiajiu Shaw; Phillip Crews
Journal:  ACS Med Chem Lett       Date:  2020-01-02       Impact factor: 4.345

3.  A reassignment of (-)-mycothiazole and the isolation of a related diol.

Authors:  Rachel N Sonnenschein; Tyler A Johnson; Karen Tenney; Frederick A Valeriote; Phillip Crews
Journal:  J Nat Prod       Date:  2006-01       Impact factor: 4.050

4.  The marine sponge metabolite mycothiazole: a novel prototype mitochondrial complex I inhibitor.

Authors:  J Brian Morgan; Fakhri Mahdi; Yang Liu; Veena Coothankandaswamy; Mika B Jekabsons; Tyler A Johnson; Koneni V Sashidhara; Phillip Crews; Dale G Nagle; Yu-Dong Zhou
Journal:  Bioorg Med Chem       Date:  2010-06-25       Impact factor: 3.641

5.  Ruthenium-Catalyzed Multicomponent Reactions: Access to α-Silyl-β-Hydroxy Vinylsilanes, Stereodefined 1,3-Dienes, and Cyclohexenes.

Authors:  Barry M Trost; Dennis C Koester; Ehesan U Sharif
Journal:  Chemistry       Date:  2016-01-25       Impact factor: 5.236

6.  Crystal structure of dimethyl 2-((2Z,5Z)-5-(2-meth-oxy-2-oxo-ethyl-idene)-2-{(E)-[2-methyl-5-(prop-1-en-2-yl)cyclo-hex-2-enyl-idene]hydrazinyl-idene}-4-oxo-thia-zolidin-3-yl)fumarate.

Authors:  Abdellah N'ait Ousidi; My Youssef Ait Itto; Aziz Auhmani; Abdelkhalek Riahi; Abdelwahed Auhmani; Jean-Claude Daran
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2017-01-31

Review 7.  Cytotoxic Compounds Derived from Marine Sponges. A Review (2010-2012).

Authors:  Roberto Mioso; Francisco J Toledo Marante; Ranilson de Souza Bezerra; Flávio Valadares Pereira Borges; Bárbara V de Oliveira Santos; Irma Herrera Bravo de Laguna
Journal:  Molecules       Date:  2017-01-28       Impact factor: 4.411
  7 in total

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