Literature DB >> 23834060

Enantioselective total synthesis and biological evaluation of (+)-kibdelone A and a tetrahydroxanthone analogue.

Dana K Winter1, Mary Ann Endoma-Arias, Tomas Hudlicky, John A Beutler, John A Porco.   

Abstract

The total synthesis of kibdelone A has been accomplished via In(III)-catalyzed arylation of a heterocyclic quinone monoketal and iodine-mediated oxidative photochemical electrocyclization for construction of the ABCD ring moiety. Enzymatic dihydroxylation of methyl 2-halobenzoate substrates was employed for synthesis of activated 2-halo-cyclohexene F-ring fragments. A one pot oxa-Michael/Friedel-Crafts process allowed access to the first simplified DEF ring analogues of the kibdelones.

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Year:  2013        PMID: 23834060      PMCID: PMC3773511          DOI: 10.1021/jo401169z

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


  21 in total

Review 1.  Xanthones from fungi, lichens, and bacteria: the natural products and their synthesis.

Authors:  Kye-Simeon Masters; Stefan Bräse
Journal:  Chem Rev       Date:  2012-05-22       Impact factor: 60.622

2.  Synthesis and biological evaluation of ABCD ring fragments of the kibdelones.

Authors:  David L Sloman; Branko Mitasev; Stephen S Scully; John A Beutler; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2011-02-18       Impact factor: 15.336

Review 3.  Xanthone derivatives: new insights in biological activities.

Authors:  M M M Pinto; M E Sousa; M S J Nascimento
Journal:  Curr Med Chem       Date:  2005       Impact factor: 4.530

4.  Total synthesis and absolute stereochemical assignment of kibdelone C.

Authors:  David L Sloman; Jeffrey W Bacon; John A Porco
Journal:  J Am Chem Soc       Date:  2011-06-15       Impact factor: 15.419

5.  Cationic iron-catalyzed intramolecular alkyne-hydroarylation with electron-deficient arenes.

Authors:  Kimihiro Komeyama; Ryoichi Igawa; Ken Takaki
Journal:  Chem Commun (Camb)       Date:  2010-01-12       Impact factor: 6.222

6.  Dioxygenase-catalysed oxidation of alkylaryl sulfides: sulfoxidation versus cis-dihydrodiol formation.

Authors:  Derek R Boyd; Narain D Sharma; Breige E Byrne; Simon A Haughey; Martina A Kennedy; Christopher C R Allen
Journal:  Org Biomol Chem       Date:  2004-08-10       Impact factor: 3.876

Review 7.  Polycyclic xanthone natural products: structure, biological activity and chemical synthesis.

Authors:  Dana K Winter; David L Sloman; John A Porco
Journal:  Nat Prod Rep       Date:  2013-01-21       Impact factor: 13.423

8.  First stereoselective total synthesis of FD-594 aglycon.

Authors:  Ritsuki Masuo; Ken Ohmori; Lukas Hintermann; Saki Yoshida; Keisuke Suzuki
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  A novel approach to 2-arylated quinolines: electrocyclization of alkynyl imines via vinylidene complexes.

Authors:  Kenichiro Sangu; Kohei Fuchibe; Takahiko Akiyama
Journal:  Org Lett       Date:  2004-02-05       Impact factor: 6.005

10.  Pt(IV)-catalyzed cyclization of arene-alkyne substrates via intramolecular electrophilic hydroarylation.

Authors:  Stefan J Pastine; So Won Youn; Dalibor Sames
Journal:  Org Lett       Date:  2003-04-03       Impact factor: 6.005

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  5 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

Review 2.  Applications of Friedel-Crafts reactions in total synthesis of natural products.

Authors:  Majid M Heravi; Vahideh Zadsirjan; Pegah Saedi; Tayebeh Momeni
Journal:  RSC Adv       Date:  2018-12-03       Impact factor: 4.036

3.  Synthesis and Biological Evaluation of Kibdelone C and Its Simplified Derivatives.

Authors:  Janjira Rujirawanich; Soyeon Kim; Ai-Jun Ma; John R Butler; Yizhong Wang; Chao Wang; Michael Rosen; Bruce Posner; Deepak Nijhawan; Joseph M Ready
Journal:  J Am Chem Soc       Date:  2016-08-09       Impact factor: 15.419

Review 4.  Benefits of Unconventional Methods in the Total Synthesis of Natural Products.

Authors:  Tomas Hudlicky
Journal:  ACS Omega       Date:  2018-12-14

5.  The Synthesis of Conjugated Bis-Aryl Vinyl Substrates and Their Photoelectrocyclization Reactions towards Phenanthrene Derivatives.

Authors:  Xuchen Zhao; Jon D Rainier
Journal:  Synthesis (Stuttg)       Date:  2021-01-11       Impact factor: 3.157

  5 in total

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