Literature DB >> 20831187

Catalytic enantioselective alkylative dearomatization-annulation: total synthesis and absolute configuration assignment of hyperibone K.

Ji Qi1, Aaron B Beeler, Qiang Zhang, John A Porco.   

Abstract

The asymmetric total synthesis of the polyprenylated acylphloroglucinol hyperibone K has been achieved using an enantioselective alkylative dearomatization-annulation process. NMR and computational studies were employed to probe the mode of action of a chiral phase-transfer (ion pair) catalyst.

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Year:  2010        PMID： 20831187      PMCID： PMC2962984          DOI： 10.1021/ja1057828

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


  21 in total

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Authors:  Naonobu Tanaka; Yoshihisa Takaishi; Yasuhiro Shikishima; Yuka Nakanishi; Kenneth Bastow; Kuo-Hsiung Lee; Gisho Honda; Michiho Ito; Yoshio Takeda; Olimjon K Kodzhimatov; Ozodbek Ashurmetov
Journal:  J Nat Prod       Date:  2004-11       Impact factor: 4.050

2.  Reverse-docking as a computational tool for the study of asymmetric organocatalysis.

Authors:  D Joseph Harriman; Ghislain Deslongchamps
Journal:  J Comput Aided Mol Des       Date:  2004-05       Impact factor: 3.686

3.  Rapid access to polyprenylated phloroglucinols via alkylative dearomatization-annulation: total synthesis of (+/-)-clusianone(1).

Authors:  Ji Qi; John A Porco
Journal:  J Am Chem Soc       Date:  2007-09-29       Impact factor: 15.419

4.  A chiral hypervalent iodine(III) reagent for enantioselective dearomatization of phenols.

Authors:  Toshifumi Dohi; Akinobu Maruyama; Naoko Takenaga; Kento Senami; Yutaka Minamitsuji; Hiromichi Fujioka; Simon B Caemmerer; Yasuyuki Kita
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Synthesis of the azaphilones using copper-mediated enantioselective oxidative dearomatization.

Authors:  Jianglong Zhu; Nicholas P Grigoriadis; Jonathan P Lee; John A Porco
Journal:  J Am Chem Soc       Date:  2005-07-06       Impact factor: 15.419

6.  Polyprenylated benzophenones from Garcinia assigu and their potential cancer chemopreventive activities.

Authors:  Chihiro Ito; Masataka Itoigawa; Yoshiaki Miyamoto; Saori Onoda; K Sundar Rao; Teruo Mukainaka; Harukuni Tokuda; Hoyoku Nishino; Hiroshi Furukawa
Journal:  J Nat Prod       Date:  2003-02       Impact factor: 4.050

7.  The enantioselective synthesis of alpha-amino acids by phase-transfer catalysis with achiral Schiff base esters.

Authors:  Martin J O'Donnell
Journal:  Acc Chem Res       Date:  2004-08       Impact factor: 22.384

8.  Kinetic resolution in a bridgehead lithiation mediated by a chiral bis-lithium amide: assignment of the absolute configuration of clusianone.

Authors:  Vincent Rodeschini; Nigel S Simpkins; Claire Wilson
Journal:  J Org Chem       Date:  2007-04-28       Impact factor: 4.354

9.  Phase-transfer-catalyzed asymmetric acylimidazole alkylation.

Authors:  Merritt B Andrus; Michael A Christiansen; Erik J Hicken; Morgan J Gainer; D Karl Bedke; Kaid C Harper; Shawn R Mikkelson; Daniel S Dodson; David T Harris
Journal:  Org Lett       Date:  2007-10-18       Impact factor: 6.005

10.  Diastereo- and enantioselective dearomatization of rhenium-bound naphthalenes.

Authors:  Fei Ding; Mark T Valahovic; Joseph M Keane; Mitchell R Anstey; Michal Sabat; Carl O Trindle; W Dean Harman
Journal:  J Org Chem       Date:  2004-04-02       Impact factor: 4.354
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  11 in total

1.  Regiodivergent Photocyclization of Dearomatized Acylphloroglucinols: Asymmetric Syntheses of (-)-Nemorosone and (-)-6-epi-Garcimultiflorone A.

Authors:  Saishuai Wen; Jonathan H Boyce; Sunil K Kandappa; Jayaraman Sivaguru; John A Porco
Journal:  J Am Chem Soc       Date:  2019-07-02       Impact factor: 15.419

2.  Total synthesis of (±)-7-epi-nemorosone.

Authors:  Qiang Zhang; John A Porco
Journal:  Org Lett       Date:  2012-03-26       Impact factor: 6.005

3.  The total synthesis of hyperpapuanone, hyperibone L, epi-clusianone and oblongifolin A.

Authors:  Nicole Biber; Katrin Möws; Bernd Plietker
Journal:  Nat Chem       Date:  2011-10-16       Impact factor: 24.427

4.  Total synthesis of plukenetione A.

Authors:  Qiang Zhang; Branko Mitasev; Ji Qi; John A Porco
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

5.  Enantioselective synthesis of tatanans A-C and reinvestigation of their glucokinase-activating properties.

Authors:  Qing Xiao; Jeffrey J Jackson; Ashok Basak; Joseph M Bowler; Brian G Miller; Armen Zakarian
Journal:  Nat Chem       Date:  2013-03-24       Impact factor: 24.427

6.  Asymmetric, stereodivergent synthesis of (-)-clusianone utilizing a biomimetic cationic cyclization.

Authors:  Jonathan H Boyce; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-10       Impact factor: 15.336

7.  Synthetic Efforts Toward [3.3.1] Bridged Bicyclic Phloroglucinol Natural Products.

Authors:  Jon T Njardarson
Journal:  Tetrahedron       Date:  2011-10-07       Impact factor: 2.457

Review 8.  An invocation for computational evaluation of isomerization transforms: cationic skeletal reorganizations as a case study.

Authors:  Alexander W Schuppe; Yannan Liu; Timothy R Newhouse
Journal:  Nat Prod Rep       Date:  2020-09-15       Impact factor: 13.423

Review 9.  Characteristic metabolites of Hypericum plants: their chemical structures and biological activities.

Authors:  Naonobu Tanaka; Yoshiki Kashiwada
Journal:  J Nat Med       Date:  2021-02-08       Impact factor: 2.343

10.  Synthesis and Multiplexed Activity Profiling of Synthetic Acylphloroglucinol Scaffolds.

Authors:  Jonathan H Boyce; Benjamin J Reisman; Brian O Bachmann; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-30       Impact factor: 15.336
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