Literature DB >> 21648477

Total synthesis and absolute stereochemical assignment of kibdelone C.

David L Sloman1, Jeffrey W Bacon, John A Porco.   

Abstract

Kibdelones are hexacyclic tetrahydroxanthones and potent anticancer agents isolated from an Australian microbe. Herein, we describe the synthesis of a chiral, nonracemic iodocyclohexene carboxylate EF ring fragment of the kibdelones employing an intramolecular iodo halo-Michael aldol reaction and its merger with an ABCD ring fragment to afford the congener kibdelone C.

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Year:  2011        PMID： 21648477      PMCID： PMC3134420          DOI： 10.1021/ja203642n

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


  32 in total

1.  Absolute configuration of kigamicins A, C and D.

Authors:  Tetsuya Someno; Setsuko Kunimoto; Hikaru Nakamura; Hiroshi Naganawa; Daishiro Ikeda
Journal:  J Antibiot (Tokyo)       Date:  2005-01       Impact factor: 2.649

2.  A mild and efficient synthesis of 4-quinolones and quinolone heterocycles.

Authors:  Daniel Zewge; Cheng-Yi Chen; Curtis Deer; Peter G Dormer; Dave L Hughes
Journal:  J Org Chem       Date:  2007-04-26       Impact factor: 4.354

3.  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

4.  The asymmetric catalytic aldol reaction of allenolates with aldehydes using n-fluoroacyl oxazaborolidine as the catalyst.

Authors:  G Li; H X Wei; B S Phelps; D W Purkiss; S H Kim
Journal:  Org Lett       Date:  2001-03-22       Impact factor: 6.005

5.  Chemical library and structure-activity relationships of 11-demethyl-12-oxo calanolide A analogues as anti-HIV-1 agents.

Authors:  Tao Ma; Li Liu; Hai Xue; Li Li; Chunyan Han; Lin Wang; Zhiwei Chen; Gang Liu
Journal:  J Med Chem       Date:  2008-02-20       Impact factor: 7.446

6.  Beta-iodoallenolates as springboards for annulation reactions.

Authors:  Jennifer Ciesielski; Daniel P Canterbury; Alison J Frontier
Journal:  Org Lett       Date:  2009-10-01       Impact factor: 6.005

7.  Kigamicins, novel antitumor antibiotics. II. Structure determination.

Authors:  Setsuko Kunimoto; Tetsuya Someno; Yohko Yamazaki; Jie Lu; Hiroyasu Esumi; Hiroshi Naganawa
Journal:  J Antibiot (Tokyo)       Date:  2003-12       Impact factor: 2.649

8.  Mild, efficient Friedel-Crafts acylations from carboxylic acids using cyanuric chloride and AlCl3.

Authors:  Cyrous O Kangani; Billy W Day
Journal:  Org Lett       Date:  2008-05-31       Impact factor: 6.005

9.  Actinoplanones C, D, E, F and G, new cytotoxic polycyclic xanthones from Actinoplanes sp.

Authors:  K Kobayashi; C Nishino; J Ohya; S Sato; T Mikawa; Y Shiobara; M Kodama
Journal:  J Antibiot (Tokyo)       Date:  1988-06       Impact factor: 2.649

10.  Structure of cervinomycin, a novel xantone antibiotic active against anaerobe and mycoplasma.

Authors:  A Nakagawa; S Omura; K Kushida; H Shimizu; G Lukacs
Journal:  J Antibiot (Tokyo)       Date:  1987-03       Impact factor: 2.649
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  13 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.  Cascade cyclizations of acyclic and macrocyclic alkynones: studies toward the synthesis of phomactin A.

Authors:  Jennifer Ciesielski; Vincent Gandon; Alison J Frontier
Journal:  J Org Chem       Date:  2013-06-10       Impact factor: 4.354

7.  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

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.  A macrocyclic β-iodoallenolate intermediate is key: synthesis of the ABD core of phomactin A.

Authors:  Jennifer Ciesielski; Kevin Cariou; Alison J Frontier
Journal:  Org Lett       Date:  2012-08-02       Impact factor: 6.005

10.  Synthetic Studies of the Rubellin Natural Products: Development of a Stereoselective Strategy and Total Synthesis of (+)-Rubellin C.

Authors:  Jackson A Gartman; Uttam K Tambar
Journal:  J Org Chem       Date:  2021-07-21       Impact factor: 4.198
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