Literature DB >> 15493911

A biomimetic approach to the rocaglamides employing photogeneration of oxidopyryliums derived from 3-hydroxyflavones.

Baudouin Gerard1, Guilford Jones Ii, John A Porco.   

Abstract

A unified biomimetic approach to the aglain-forbaglin-rocaglamide classes of natural products is reported. The approach involves photogeneration of oxidopyryliums via excited-state intramolecular proton transfer (ESIPT) of 3-hydroxyflavones followed by [3+2] dipolar cycloaddition to the aglain core. An alpha-ketol (acyloin) rearrangement was employed to transform the aglain core to the rocaglamide framework. This approach was successfully used for the synthesis of the natural product (+/-)-methyl rocaglate.

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Year:  2004        PMID： 15493911     DOI： 10.1021/ja044798o

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


  21 in total

1.  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

Review 2.  Chemical probes and drug leads from advances in synthetic planning and methodology.

Authors:  Christopher J Gerry; Stuart L Schreiber
Journal:  Nat Rev Drug Discov       Date:  2018-04-13       Impact factor: 84.694

Review 3.  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

4.  Enantioselective photocycloaddition of 3-hydroxyflavones: total syntheses and absolute configuration assignments of (+)-ponapensin and (+)-elliptifoline.

Authors:  Neil J Lajkiewicz; Stéphane P Roche; Baudouin Gerard; John A Porco
Journal:  J Am Chem Soc       Date:  2012-07-25       Impact factor: 15.419

5.  A photochemical flow reactor for large scale syntheses of aglain and rocaglate natural product analogues.

Authors:  Han Yueh; Qiwen Gao; John A Porco; Aaron B Beeler
Journal:  Bioorg Med Chem       Date:  2017-06-11       Impact factor: 3.641

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.  Total Syntheses of the Isomeric Aglain Natural Products Foveoglin A and Perviridisin B: Selective Excited-State Intramolecular Proton-Transfer Photocycloaddition.

Authors:  Wenyu Wang; Anthony Clay; Retheesh Krishnan; Neil J Lajkiewicz; Lauren E Brown; Jayaraman Sivaguru; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-13       Impact factor: 15.336

9.  Vinylogous addition of siloxyfurans to benzopyryliums: a concise approach to the tetrahydroxanthone natural products.

Authors:  Tian Qin; Richard P Johnson; John A Porco
Journal:  J Am Chem Soc       Date:  2011-01-25       Impact factor: 15.419

10.  Oxidopyrylium [5+2] Cycloaddition Chemistry: Historical Perspective and Recent Advances (2008-2018).

Authors:  Lauren P Bejcek; Ryan P Murelli
Journal:  Tetrahedron       Date:  2018-04-05       Impact factor: 2.457
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