Literature DB >> 21648478

Enantioselective total synthesis of (-)-kibdelone C.

John R Butler1, Chao Wang, Jianwei Bian, Joseph M Ready.   

Abstract

The kibdelones are aromatic polyketide natural products featuring isoquinolinone and tetrahydroxanthone ring systems. They display potent cytotoxicity toward a range of human cancer cell lines. Here, we present an enantioselective total synthesis of kibdelone C that utilizes a Shi epoxidation to establish the absolute and relative stereochemistry, an acid-catalyzed cyclization to form the tetrahydroxanthone, and a C-H arylation to complete the hexacyclic skeleton.

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Year:  2011        PMID: 21648478     DOI: 10.1021/ja204040k

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  10 in total

Review 1.  Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors:  K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal:  Chem Soc Rev       Date:  2012-06-28       Impact factor: 54.564

2.  Total Synthesis of the Aglycone of IB-00208.

Authors:  Daniel Knueppel; Jingyue Yang; Bo Cheng; Douglas Mans; Stephen F Martin
Journal:  Tetrahedron       Date:  2015-09-02       Impact factor: 2.457

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

Authors:  Dana K Winter; Mary Ann Endoma-Arias; Tomas Hudlicky; John A Beutler; John A Porco
Journal:  J Org Chem       Date:  2013-07-23       Impact factor: 4.354

4.  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 5.  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

6.  Dehydrogenative coupling to enable the enantioselective total synthesis of (-)-simaomicin α.

Authors:  Yizhong Wang; Chao Wang; John R Butler; Joseph M Ready
Journal:  Angew Chem Int Ed Engl       Date:  2013-08-22       Impact factor: 15.336

7.  Syntheses of Dimeric Tetrahydroxanthones with Varied Linkages: Investigation of "Shapeshifting" Properties.

Authors:  Tian Qin; Takayuki Iwata; Tanya T Ransom; John A Beutler; John A Porco
Journal:  J Am Chem Soc       Date:  2015-11-25       Impact factor: 15.419

8.  Enantioselective Halolactonization Reactions using BINOL-Derived Bifunctional Catalysts: Methodology, Diversification, and Applications.

Authors:  Daniel W Klosowski; J Caleb Hethcox; Daniel H Paull; Chao Fang; James R Donald; Christopher R Shugrue; Andrew D Pansick; Stephen F Martin
Journal:  J Org Chem       Date:  2018-05-22       Impact factor: 4.354

9.  Co-catalyzed ortho-C-H functionalization/annulation of arenes and alkenes with alkynylsilanes: access to isoquinolone and pyridone motifs.

Authors:  Cong Lin; Liang Shen
Journal:  RSC Adv       Date:  2019-09-26       Impact factor: 4.036

10.  Approaches to polycyclic 1,4-dioxygenated xanthones. Application to total synthesis of the aglycone of IB-00208.

Authors:  Jingyue Yang; Daniel Knueppel; Bo Cheng; Douglas Mans; Stephen F Martin
Journal:  Org Lett       Date:  2014-12-16       Impact factor: 6.005

  10 in total

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