Literature DB >> 19445456

Nazarov cyclization initiated by peracid oxidation: the total synthesis of (+/-)-rocaglamide.

John A Malona1, Kevin Cariou, Alison J Frontier.   

Abstract

The total syntheses of aglafolin, rocagloic acid, and rocaglamide using Nazarov cyclization are described. Generation of the necessary oxyallyl cation intermediate was accomplished via peracid oxidation of an allenol ether to generate an unusual oxycarbenium ion species that undergoes cyclization. The synthesis is efficient, highly diastereoselective, and strategically distinct from previous syntheses of rocaglamide.

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Year:  2009        PMID： 19445456      PMCID： PMC2732401          DOI： 10.1021/ja9029736

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


  11 in total

1.  Stereospecific synthesis of (+/-)-1,2-anhydro methyl rocaglate.

Authors:  Philip Magnus; Matthew A H Stent
Journal:  Org Lett       Date:  2005-09-01       Impact factor: 6.005

2.  Intramolecular azide trapping of the Nazarov intermediate: formation of peroxy-bridged indolizidinones via a deep-seated rearrangement and aerobic oxidation.

Authors:  Ali Rostami; Yong Wang; Atta M Arif; Robert McDonald; F G West
Journal:  Org Lett       Date:  2007-01-26       Impact factor: 6.005

3.  Total synthesis of (-)-episilvestrol and (-)-silvestrol.

Authors:  Mariana El Sous; Mui Ling Khoo; Georgina Holloway; David Owen; Peter J Scammells; Mark A Rizzacasa
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  Asymmetric amine-intercepted Nazarov cyclization.

Authors:  Francis Dhoro; Tor E Kristensen; Vegar Stockmann; Glenn P A Yap; Marcus A Tius
Journal:  J Am Chem Soc       Date:  2007-05-18       Impact factor: 15.419

5.  Enantioselective photocycloaddition mediated by chiral Brønsted acids: asymmetric synthesis of the rocaglamides.

Authors:  Baudouin Gerard; Sheharbano Sangji; Daniel J O'Leary; John A Porco
Journal:  J Am Chem Soc       Date:  2006-06-21       Impact factor: 15.419

6.  Polarizing the Nazarov cyclization: the impact of dienone substitution pattern on reactivity and selectivity.

Authors:  Wei He; Ildiko R Herrick; Tulay A Atesin; Patrick A Caruana; Colleen A Kellenberger; Alison J Frontier
Journal:  J Am Chem Soc       Date:  2008-01-23       Impact factor: 15.419

7.  Synthesis of 5-hydroxycyclopent-2-enones from allenyl vinyl ketones via an interrupted Nazarov cyclization.

Authors:  Vanessa M Marx; D Jean Burnell
Journal:  Org Lett       Date:  2009-03-19       Impact factor: 6.005

8.  The traditional Chinese herbal compound rocaglamide preferentially induces apoptosis in leukemia cells by modulation of mitogen-activated protein kinase activities.

Authors:  Jia Y Zhu; Inna N Lavrik; Ulrich Mahlknecht; Marco Giaisi; Peter Proksch; Peter H Krammer; Min Li-Weber
Journal:  Int J Cancer       Date:  2007-10-15       Impact factor: 7.396

9.  Theoretical study of the vinyl allene oxide to cyclopent-2-en-1-one rearrangement: mechanism, torquoselectivity and solvent effects.

Authors:  Carlos Silva López; Olalla Nieto Faza; Darrin M York; Angel R de Lera
Journal:  J Org Chem       Date:  2004-05-28       Impact factor: 4.354

10.  Polarizing the Nazarov cyclization: efficient catalysis under mild conditions.

Authors:  Wei He; Xiufeng Sun; Alison J Frontier
Journal:  J Am Chem Soc       Date:  2003-11-26       Impact factor: 15.419
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  25 in total

1.  Using Nazarov electrocyclization to stage chemoselective [1,2]-migrations: stereoselective synthesis of functionalized cyclopentenones.

Authors:  David Lebœuf; Jie Huang; Vincent Gandon; Alison J Frontier
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-26       Impact factor: 15.336

2.  Total synthesis of (±)-rocaglamide via oxidation-initiated Nazarov cyclization.

Authors:  John A Malona; Kevin Cariou; William T Spencer; Alison J Frontier
Journal:  J Org Chem       Date:  2012-01-26       Impact factor: 4.354

3.  A highly reactive dicationic iridium(III) catalyst for the polarized Nazarov cyclization reaction.

Authors:  Tulaza Vaidya; Abdurrahman C Atesin; Ildiko R Herrick; Alison J Frontier; Richard Eisenberg
Journal:  Angew Chem Int Ed Engl       Date:  2010-04-26       Impact factor: 15.336

Review 4.  Chemistry and biology of rocaglamides (= flavaglines) and related derivatives from aglaia species (meliaceae).

Authors:  Sherif S Ebada; Neil Lajkiewicz; John A Porco; Min Li-Weber; Peter Proksch
Journal:  Prog Chem Org Nat Prod       Date:  2011

5.  Experimental and theoretical studies on the Nazarov cyclization/Wagner-Meerwein rearrangement sequence.

Authors:  David Lebœuf; Vincent Gandon; Jennifer Ciesielski; Alison J Frontier
Journal:  J Am Chem Soc       Date:  2012-04-03       Impact factor: 15.419

Review 6.  Rocaglamide, silvestrol and structurally related bioactive compounds from Aglaia species.

Authors:  Li Pan; John L Woodard; David M Lucas; James R Fuchs; A Douglas Kinghorn
Journal:  Nat Prod Rep       Date:  2014-05-02       Impact factor: 13.423

7.  Biomimetic photocycloaddition of 3-hydroxyflavones: synthesis and evaluation of rocaglate derivatives as inhibitors of eukaryotic translation.

Authors:  Stéphane P Roche; Regina Cencic; Jerry Pelletier; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2010-09-03       Impact factor: 15.336

8.  Cycloaromatization protocol for synthesis of polysubstituted phenol derivatives: method development and mechanistic studies.

Authors:  William T Spencer; Alison J Frontier
Journal:  J Org Chem       Date:  2012-08-14       Impact factor: 4.354

9.  Flavaglines target primitive leukemia cells and enhance anti-leukemia drug activity.

Authors:  K P Callahan; M Minhajuddin; C Corbett; E D Lagadinou; R M Rossi; V Grose; M M Balys; L Pan; S Jacob; A Frontier; M R Grever; D M Lucas; A D Kinghorn; J L Liesveld; M W Becker; C T Jordan
Journal:  Leukemia       Date:  2014-02-28       Impact factor: 11.528

10.  α-Aryl-substituted allenamides in an imino-Nazarov cyclization cascade catalyzed by Au(I).

Authors:  Zhi-Xiong Ma; Shuzhong He; Wangze Song; Richard P Hsung
Journal:  Org Lett       Date:  2012-11-02       Impact factor: 6.005
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