Literature DB >> 22360604

Enantioselective total synthesis of (S)-bisoranjidiol, an axially chiral bisanthraquinone.

Erin E Podlesny1, Marisa C Kozlowski.   

Abstract

The first enantioselective total synthesis of the bisanthraquinone (S)-bisoranjidiol and an unnatural regioisomer has been accomplished. Key features of the synthesis include the asymmetric oxidative biaryl coupling of a hindered 8-substituted 2-naphthol, selective para-quinone formation, and regioselective tandem Diels-Alder/aromatization reactions.

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Year:  2012        PMID： 22360604      PMCID： PMC3306814          DOI： 10.1021/ol3001365

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


  29 in total

1.  Novel pathways for the formation of chiral binaphthyl polymers: oxidative asymmetric phenolic coupling alone and in tandem with the Glaser-Hay coupling.

Authors:  Xu Xie; Puay-Wah Phuan; Marisa C Kozlowski
Journal:  Angew Chem Int Ed Engl       Date:  2003-05-16       Impact factor: 15.336

2.  Metabolic products of fungi. XIV. The structure of skyrin. III. On pseudoskyrin.

Authors:  O TANAKA
Journal:  Chem Pharm Bull (Tokyo)       Date:  1958-04       Impact factor: 1.645

3.  The cytoskyrin cascade: a facile entry into cytoskyrin A, deoxyrubroskyrin, rugulin, skyrin, and flavoskyrin model systems.

Authors:  K C Nicolaou; Charles D Papageorgiou; Jared L Piper; Raj K Chadha
Journal:  Angew Chem Int Ed Engl       Date:  2005-09-12       Impact factor: 15.336

4.  Anthraquinone derivatives from Heterophyllaea pustulata.

Authors:  Susana C Núñez Montoya; Alicia M Agnese; José L Cabrera
Journal:  J Nat Prod       Date:  2006-05       Impact factor: 4.050

5.  Total syntheses of 2,2'-epi-cytoskyrin A, rugulosin, and the alleged structure of rugulin.

Authors:  K C Nicolaou; Yee Hwee Lim; Jared L Piper; Charles D Papageorgiou
Journal:  J Am Chem Soc       Date:  2007-03-14       Impact factor: 15.419

6.  Asymmetric total synthesis of nigerone.

Authors:  Evan S Divirgilio; Elizabeth C Dugan; Carol A Mulrooney; Marisa C Kozlowski
Journal:  Org Lett       Date:  2007-02-01       Impact factor: 6.005

7.  Enantioselective oxidative biaryl coupling reactions catalyzed by 1,5-diazadecalin metal complexes.

Authors:  X Li; J Yang; M C Kozlowski
Journal:  Org Lett       Date:  2001-04-19       Impact factor: 6.005

8.  Design, synthesis, and investigation of protein kinase C inhibitors: total syntheses of (+)-calphostin D, (+)-phleichrome, cercosporin, and new photoactive perylenequinones.

Authors:  Barbara J Morgan; Sangeeta Dey; Steven W Johnson; Marisa C Kozlowski
Journal:  J Am Chem Soc       Date:  2009-07-08       Impact factor: 15.419

9.  Phototoxic effects of Heterophyllaea pustulata (Rubiaceae).

Authors:  Susana C Núñez Montoya; Laura R Comini; Belén Rumie Vittar; Ivana M Fernández; Viviana A Rivarola; José L Cabrera
Journal:  Toxicon       Date:  2008-03-13       Impact factor: 3.033

10.  Metabolic products of fungi. VI. The structure of skyrin. II. Synthesis of skyrin beta, beta'-dimethyl ether.

Authors:  O TANAKA; C KANEKO
Journal:  Pharm Bull       Date:  1955-08
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  5 in total

Review 1.  Aerobic copper-catalyzed organic reactions.

Authors:  Scott E Allen; Ryan R Walvoord; Rosaura Padilla-Salinas; Marisa C Kozlowski
Journal:  Chem Rev       Date:  2013-06-20       Impact factor: 60.622

2.  Selective oxidation of 8,8'-hydroxylated binaphthols to bis-spironaphthalenones or binaphtho-para- and binaphtho-ortho-quinones.

Authors:  Erin E Podlesny; Patrick J Carroll; Marisa C Kozlowski
Journal:  Org Lett       Date:  2012-08-31       Impact factor: 6.005

3.  Structural reassignment of a marine metabolite from a binaphthalenetetrol to a tetrabrominated diphenyl ether.

Authors:  Erin E Podlesny; Marisa C Kozlowski
Journal:  J Nat Prod       Date:  2012-06-12       Impact factor: 4.050

4.  Recent total syntheses of anthraquinone-based natural products.

Authors:  Jackson A Gartman; Uttam K Tambar
Journal:  Tetrahedron       Date:  2022-01-11       Impact factor: 2.457

5.  Divergent approach to the bisanthraquinone natural products: total synthesis of (S)-bisoranjidiol and derivatives from binaphtho-para-quinones.

Authors:  Erin E Podlesny; Marisa C Kozlowski
Journal:  J Org Chem       Date:  2013-01-04       Impact factor: 4.354
  5 in total

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