Literature DB >> 28950418

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

Wenyu Wang1, Anthony Clay2, Retheesh Krishnan3, Neil J Lajkiewicz1, Lauren E Brown1, Jayaraman Sivaguru2, John A Porco1.   

Abstract

Selective excited-state intramolecular proton-transfer (ESIPT) photocycloaddition of 3-hydroxyflavones with trans, trans-1,4-diphenyl-1,3-butadiene is described. Using this methodology, total syntheses of the natural products (±)-foveoglin A and (±)-perviridisin B were accomplished. Enantioselective ESIPT photocycloaddition using TADDOLs as chiral hydrogen-bonding additives provided access to (+)-foveoglin A. Mechanistic studies have revealed the possibility for a photoinduced electron-transfer (PET) pathway.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric synthesis; electron transfer; natural products; photochemistry; total synthesis

Mesh：

Substances：

Year:  2017        PMID： 28950418      PMCID： PMC5876029          DOI： 10.1002/anie.201707539

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  28 in total

1.  Molecular oxygen as a redox catalyst in intramolecular photocycloadditions of coumarins.

Authors:  Darius Paul Kranz; Axel Georg Griesbeck; Ronald Alle; Raul Perez-Ruiz; Jörg Martin Neudörfl; Klaus Meerholz; Hans-Günther Schmalz
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-03       Impact factor: 15.336

2.  Photochemical activity of a key donor-acceptor complex can drive stereoselective catalytic α-alkylation of aldehydes.

Authors:  Elena Arceo; Igor D Jurberg; Ana Alvarez-Fernández; Paolo Melchiorre
Journal:  Nat Chem       Date:  2013-08-11       Impact factor: 24.427

Review 3.  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

4.  Enantioselective catalysis of the intermolecular [2+2] photocycloaddition between 2-pyridones and acetylenedicarboxylates.

Authors:  Mark M Maturi; Thorsten Bach
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-02       Impact factor: 15.336

5.  Visible-light excitation of iminium ions enables the enantioselective catalytic β-alkylation of enals.

Authors:  Mattia Silvi; Charlie Verrier; Yannick P Rey; Luca Buzzetti; Paolo Melchiorre
Journal:  Nat Chem       Date:  2017-03-20       Impact factor: 24.427

6.  Constituents of the Leaves and Stem Bark of Aglaia foveolata.

Authors:  Angela A Salim; Hee-Byung Chai; Ismail Rachman; Soedarsono Riswan; Leonardus B S Kardono; Norman R Farnsworth; Esperanza J Carcache-Blanco; A Douglas Kinghorn
Journal:  Tetrahedron       Date:  2007-08-13       Impact factor: 2.457

7.  Synthetic analogue of rocaglaol displays a potent and selective cytotoxicity in cancer cells: involvement of apoptosis inducing factor and caspase-12.

Authors:  Frédéric Thuaud; Yohann Bernard; Gülen Türkeri; Ronan Dirr; Geneviève Aubert; Thierry Cresteil; Aurélie Baguet; Catherine Tomasetto; Yuri Svitkin; Nahum Sonenberg; Canan G Nebigil; Laurent Désaubry
Journal:  J Med Chem       Date:  2009-08-27       Impact factor: 7.446

8.  Synthesis of Aza-Rocaglates via ESIPT-Mediated (3+2) Photocycloaddition.

Authors:  Wenyu Wang; Regina Cencic; Luke Whitesell; Jerry Pelletier; John A Porco
Journal:  Chemistry       Date:  2016-07-15       Impact factor: 5.236

Review 9.  Flavaglines: potent anticancer drugs that target prohibitins and the helicase eIF4A.

Authors:  Christine Basmadjian; Frédéric Thuaud; Nigel Ribeiro; Laurent Désaubry
Journal:  Future Med Chem       Date:  2013-12       Impact factor: 3.808

10.  Translation Inhibition by Rocaglates Is Independent of eIF4E Phosphorylation Status.

Authors:  Jennifer Chu; Regina Cencic; Wenyu Wang; John A Porco; Jerry Pelletier
Journal:  Mol Cancer Ther       Date:  2015-11-19       Impact factor: 6.261
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  6 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.  Intercepted Retro-Nazarov Reaction: Syntheses of Amidino-Rocaglate Derivatives and Their Biological Evaluation as eIF4A Inhibitors.

Authors:  Wenhan Zhang; Jennifer Chu; Andrew M Cyr; Han Yueh; Lauren E Brown; Tony T Wang; Jerry Pelletier; John A Porco
Journal:  J Am Chem Soc       Date:  2019-07-30       Impact factor: 15.419

Review 3.  Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry.

Authors:  Laura Buglioni; Fabian Raymenants; Aidan Slattery; Stefan D A Zondag; Timothy Noël
Journal:  Chem Rev       Date:  2021-08-10       Impact factor: 60.622

Review 4.  Enantioselective synthesis of heterocyclic compounds using photochemical reactions.

Authors:  Norbert Hoffmann
Journal:  Photochem Photobiol Sci       Date:  2021-11-25       Impact factor: 3.982

5.  An efficient Nozaki-Hiyama allenylation promoted by the acid derived MIL-101 MOF.

Authors:  Yi Luan; Zonghui Cai; Xiujuan Li; Daniele Ramella; Zongcheng Miao; Wenyu Wang
Journal:  RSC Adv       Date:  2019-03-07       Impact factor: 4.036

6.  Chemical Synthesis Enables Structural Reengineering of Aglaroxin C Leading to Inhibition Bias for Hepatitis C Viral Infection.

Authors:  Wenhan Zhang; Shufeng Liu; Rayelle I Maiga; Jerry Pelletier; Lauren E Brown; Tony T Wang; John A Porco
Journal:  J Am Chem Soc       Date:  2019-01-11       Impact factor: 15.419
  6 in total

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