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FRESCO SIGNED

Efficient, Flexible Synthesis of Molecules with Tailored Shapes: from Photo-switchable Helices to anti-Cancer Compounds

Total Cost €

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EC-Contrib. €

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Partnership

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 FRESCO project word cloud

Explore the words cloud of the FRESCO project. It provides you a very rough idea of what is the project "FRESCO" about.

forming    interactions    full    switched    pot    synthesis    homologated    medicine    stereocontrol    reaction    gt    robustness    conduct    solid    light    found    ripe    iteratively    creation    strategy    efficiency    repeat    iterations    active    preparation    carbon    libraries    controls    shows    disrupt    classes    shape    stereochemistry    methodology    central    broad    give    chirality    spectrum    conformation    progress    groups    98    turn    organic    limited    reliably    amongst    structures    demonstrated    subsequent    units    combining    functionalised    ready    sense    blocks    complete    fundamentally    proposing    diverse    lithiated    chain    biologically    disciplines    difficulties    boronic    dialled    protein    cancer    ester    scope    provides    transfer    binding    entities    polyketides    helical    polypropionates    materials    carbamate    chemical    bond    borylation    family    assembly    places    explore    selective    building    molecular    lithiation    rapid    extend    natural    revolutionise    basic    optimum    line    molecules    carbamates    prepare   

Project "FRESCO" data sheet

The following table provides information about the project.

Coordinator
UNIVERSITY OF BRISTOL 

Organization address
address: BEACON HOUSE QUEENS ROAD
city: BRISTOL
postcode: BS8 1QU
website: www.bristol.ac.uk

contact info
title: n.a.
name: n.a.
surname: n.a.
function: n.a.
email: n.a.
telephone: n.a.
fax: n.a.

 Coordinator Country United Kingdom [UK]
 Project website http://www.chm.bris.ac.uk/org/aggarwal/
 Total cost 2˙436˙379 €
 EC max contribution 2˙436˙379 € (100%)
 Programme 1. H2020-EU.1.1. (EXCELLENT SCIENCE - European Research Council (ERC))
 Code Call ERC-2014-ADG
 Funding Scheme ERC-ADG
 Starting year 2015
 Duration (year-month-day) from 2015-10-01   to  2020-09-30

 Partnership

Take a look of project's partnership.

# participants  country  role  EC contrib. [€] 
1    UNIVERSITY OF BRISTOL UK (BRISTOL) coordinator 2˙436˙379.00

Map

 Project objective

The creation of new molecular entities and subsequent exploitation of their properties is central to a broad spectrum of research disciplines from medicine to materials but progress has been limited by the difficulties associated with chemical synthesis. We are now proposing a fundamentally new strategy, which has the potential to revolutionise how we conduct complex organic synthesis. The basic C–C bond-forming step involves the reaction of a lithiated carbamate with a boronic ester to give a homologated boronic ester with complete stereocontrol. Furthermore, the reaction shows >98% efficiency in most cases and can be conducted iteratively and in one pot (up to 9 iterations has been demonstrated with full stereocontrol). We will now extend this methodology to more functionalised carbamates as this will enable the rapid synthesis of polypropionates, which are amongst the most important classes of biologically active molecules. The robust methodology is now ripe for transfer to the solid phase as this will enable the preparation of libraries of these molecules. Through applying our assembly-line-synthesis methodology to complex molecules with diverse structures, we will demonstrate its scope, robustness, and full potential. The methodology enables stereochemistry to be ‘dialled in’ to a carbon chain, which in turn controls the conformation and we will exploit this feature in the shape-selective synthesis of molecules. We will explore how the sense of helical chirality of these molecules can be switched (M to P) just with light. We will target helical molecules with specific groups at specific places for optimum binding to disrupt protein–protein interactions involved in cancer. Finally, our methodology provides ready access to a family of building blocks that represent common repeat units found in polyketides. By combining these building blocks iteratively using lithiation-borylation, we should be able to rapidly and reliably prepare complex natural products.

 Publications

year authors and title journal last update
List of publications.
2020 Johan A. Pradeilles, Siying Zhong, Márton Baglyas, György Tarczay, Craig P. Butts, Eddie L. Myers, Varinder K. Aggarwal
Odd–even alternations in helical propensity of a homologous series of hydrocarbons
published pages: , ISSN: 1755-4330, DOI: 10.1038/s41557-020-0429-0
Nature Chemistry 2020-04-15
2019 Jingjing Wu, Phillip S. Grant, Xiabing Li, Adam Noble, Varinder K. Aggarwal
Catalyst‐Free Deaminative Functionalizations of Primary Amines by Photoinduced Single‐Electron Transfer
published pages: 5697-5701, ISSN: 1433-7851, DOI: 10.1002/anie.201814452
Angewandte Chemie International Edition 58/17 2020-04-15
2019 Charlotte H. U. Gregson, Venkataraman Ganesh, Varinder K. Aggarwal
Strain Release of Donor–Acceptor Cyclopropyl Boronate Complexes
published pages: 3412-3416, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.9b01152
Organic Letters 21/9 2020-04-15
2019 Jingjing Wu, Robin M. Bär, Lin Guo, Adam Noble, Varinder K. Aggarwal
Photoinduced Deoxygenative Borylations of Aliphatic Alcohols
published pages: 18830-18834, ISSN: 1433-7851, DOI: 10.1002/anie.201910051
Angewandte Chemie International Edition 58/52 2020-04-15
2019 Chao Shu, Adam Noble, Varinder K. Aggarwal
Photoredox‐Catalyzed Cyclobutane Synthesis by a Deboronative Radical Addition–Polar Cyclization Cascade
published pages: 3870-3874, ISSN: 1433-7851, DOI: 10.1002/anie.201813917
Angewandte Chemie International Edition 58/12 2020-04-15
2020 Riccardo S. Mega, Vincent K. Duong, Adam Noble, Varinder K. Aggarwal
Decarboxylative Conjunctive Cross‐coupling of Vinyl Boronic Esters using Metallaphotoredox Catalysis
published pages: 4375-4379, ISSN: 1433-7851, DOI: 10.1002/anie.201916340
Angewandte Chemie International Edition 59/11 2020-04-15
2019 Alexander Fawcett, Tobias Biberger, Varinder K. Aggarwal
Carbopalladation of C–C σ-bonds enabled by strained boronate complexes
published pages: 117-122, ISSN: 1755-4330, DOI: 10.1038/s41557-018-0181-x
Nature Chemistry 11/2 2020-04-15
2019 Daniel Kaiser, Adam Noble, Valerio Fasano, Varinder K. Aggarwal
1,2-Boron Shifts of β-Boryl Radicals Generated from Bis-boronic Esters Using Photoredox Catalysis
published pages: 14104-14109, ISSN: 0002-7863, DOI: 10.1021/jacs.9b07564
Journal of the American Chemical Society 141/36 2020-04-15
2019 Alexander Fawcett, Amna Murtaza, Charlotte H. U. Gregson, Varinder K. Aggarwal
Strain-Release-Driven Homologation of Boronic Esters: Application to the Modular Synthesis of Azetidines
published pages: 4573-4578, ISSN: 0002-7863, DOI: 10.1021/jacs.9b01513
Journal of the American Chemical Society 141/11 2020-04-15
2017 Varinder Aggarwal, Roly Armstrong
50 Years of Zweifel Olefination: A Transition-Metal-Free Coupling
published pages: 3323-3336, ISSN: 0039-7881, DOI: 10.1055/s-0036-1589046
Synthesis 49/15 2019-07-05
2017 Daniel J. Blair, Damiano Tanini, Joseph M. Bateman, Helen K. Scott, Eddie L. Myers, Varinder K. Aggarwal
Selective uni- and bidirectional homologation of diborylmethane
published pages: 2898-2903, ISSN: 2041-6520, DOI: 10.1039/C6SC05338F
Chem. Sci. 8/4 2019-07-05
2018 Jingjing Wu, Lin He, Adam Noble, Varinder K. Aggarwal
Photoinduced Deaminative Borylation of Alkylamines
published pages: 10700–10704, ISSN: 0002-7863, DOI: 10.1021/jacs.8b07103
Journal of the American Chemical Society 140 2019-07-05
2017 Teerawut Bootwicha, Julian M. Feilner, Eddie L. Myers, Varinder K. Aggarwal
Iterative assembly line synthesis of polypropionates with full stereocontrol
published pages: , ISSN: 1755-4330, DOI: 10.1038/nchem.2757
Nature Chemistry 2019-07-05
2016 D. J. Blair, S. Zhong, M. J. Hesse, N. Zabaleta, E. L. Myers, V. K. Aggarwal
Full chirality transfer in the synthesis of hindered tertiary boronic esters under in situ lithiation–borylation conditions
published pages: 5289-5292, ISSN: 1359-7345, DOI: 10.1039/C6CC00536E
Chem. Commun. 52/30 2019-07-05
2018 Adam Noble, Riccardo S. Mega, Daniel Pflästerer, Eddie L. Myers, Varinder K. Aggarwal
Visible-Light-Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ-Amino Boronic Esters
published pages: 2155-2159, ISSN: 1433-7851, DOI: 10.1002/anie.201712186
Angewandte Chemie International Edition 57/8 2019-07-05
2017 Alexander Fawcett, Johan Pradeilles, Yahui Wang, Tatsuya Mutsuga, Eddie L. Myers, Varinder K. Aggarwal
Photoinduced decarboxylative borylation of carboxylic acids
published pages: 283-286, ISSN: 0036-8075, DOI: 10.1126/science.aan3679
Science 357/6348 2019-07-05
2017 James R. Smith, Beatrice S. L. Collins, Matthew J. Hesse, Mark A. Graham, Eddie L. Myers, Varinder K. Aggarwal
Enantioselective Rhodium(III)-Catalyzed Markovnikov Hydroboration of Unactivated Terminal Alkenes
published pages: 9148-9151, ISSN: 0002-7863, DOI: 10.1021/jacs.7b05149
Journal of the American Chemical Society 139/27 2019-07-05
2018 Oleksandr Zhurakovskyi, Yunus E. Türkmen, Lorenz E. Löffler, Vijayalakshmi A. Moorthie, C. Chun Chen, Michael A. Shaw, Mark R. Crimmin, Marco Ferrara, Mushtaq Ahmad, Mehrnoosh Ostovar, Johnathan V. Matlock, Varinder K. Aggarwal
Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides
published pages: 1346-1350, ISSN: 1433-7851, DOI: 10.1002/anie.201712065
Angewandte Chemie International Edition 57/5 2019-07-05
2017 Giorgia Casoni, Murat Kucukdisli, James M. Fordham, Matthew Burns, Eddie L. Myers, Varinder K. Aggarwal
α-Sulfinyl Benzoates as Precursors to Li and Mg Carbenoids for the Stereoselective Iterative Homologation of Boronic Esters
published pages: 11877-11886, ISSN: 0002-7863, DOI: 10.1021/jacs.7b05457
Journal of the American Chemical Society 139/34 2019-07-05
2018 Mattia Silvi, Raffael Schrof, Adam Noble, Varinder K. Aggarwal
Enantiospecific Three-Component Alkylation of Furan and Indole
published pages: 4279-4282, ISSN: 0947-6539, DOI: 10.1002/chem.201800527
Chemistry - A European Journal 24/17 2019-07-05
2017 Cristina García-Ruiz, Jack L.-Y. Chen, Christopher Sandford, Kathryn Feeney, Paula Lorenzo, Guillaume Berionni, Herbert Mayr, Varinder K. Aggarwal
Stereospecific Allylic Functionalization: The Reactions of Allylboronate Complexes with Electrophiles
published pages: 15324-15327, ISSN: 0002-7863, DOI: 10.1021/jacs.7b10240
Journal of the American Chemical Society 139/43 2019-07-05
2017 Beatrice S. L. Collins, Claire M. Wilson, Eddie L. Myers, Varinder K. Aggarwal
Asymmetric Synthesis of Secondary and Tertiary Boronic Esters
published pages: 11700-11733, ISSN: 1433-7851, DOI: 10.1002/anie.201701963
Angewandte Chemie International Edition 56/39 2019-07-05
2017 Jingjing Wu, Paula Lorenzo, Siying Zhong, Muhammad Ali, Craig P. Butts, Eddie L. Myers, Varinder K. Aggarwal
Synergy of synthesis, computation and NMR reveals correct baulamycin structures
published pages: 436-440, ISSN: 0028-0836, DOI: 10.1038/nature23265
Nature 547/7664 2019-07-05
2017 Claire M. Wilson, Venkataraman Ganesh, Adam Noble, Varinder K. Aggarwal
Enantiospecific sp 2 -sp 3 Coupling of ortho - and para -Phenols with Secondary and Tertiary Boronic Esters
published pages: 16318-16322, ISSN: 1433-7851, DOI: 10.1002/anie.201710777
Angewandte Chemie International Edition 56/51 2019-07-05
2017 Christopher Sandford, Varinder K. Aggarwal
Stereospecific functionalizations and transformations of secondary and tertiary boronic esters
published pages: 5481-5494, ISSN: 1359-7345, DOI: 10.1039/C7CC01254C
Chem. Commun. 53/40 2019-07-05
2018 Oleksandr Zhurakovskyi, Rafael M. P. Dias, Adam Noble, Varinder K. Aggarwal
Stereo- and Regiocontrolled Methylboration of Terminal Alkynes
published pages: 3136-3139, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.8b01252
Organic Letters 20/10 2019-07-05
2017 Stefan Aichhorn, Raphael Bigler, Eddie L. Myers, Varinder K. Aggarwal
Enantiospecific Synthesis of ortho -Substituted Benzylic Boronic Esters by a 1,2-Metalate Rearrangement/1,3-Borotropic Shift Sequence
published pages: 9519-9522, ISSN: 0002-7863, DOI: 10.1021/jacs.7b05880
Journal of the American Chemical Society 139/28 2019-07-05
2018 Alba Millán, Pablo D. Grigol Martinez, Varinder K. Aggarwal
Stereocontrolled Synthesis of Polypropionate Fragments based on a Building Block Assembly Strategy using Lithiation-Borylation Methodologies
published pages: 730-735, ISSN: 0947-6539, DOI: 10.1002/chem.201704946
Chemistry - A European Journal 24/3 2019-07-05
2018 Rory C. Mykura, Simon Veth, Ana Varela, Lydia Dewis, Joshua J. Farndon, Eddie L. Myers, Varinder K. Aggarwal
Investigation of the Deprotonative Generation and Borylation of Diamine-Ligated α-Lithiated Carbamates and Benzoates by in Situ IR spectroscopy
published pages: 14677-14686, ISSN: 0002-7863, DOI: 10.1021/jacs.8b06871
Journal of the American Chemical Society 140/44 2019-04-18
2018 Varinder Aggarwal, Chloe Tillin, Raphael Bigler, Renata Calo-Lapido, Beatrice Collins, Adam Noble
Complex Boron-Containing Molecules through a 1,2-Metalate Rearrangement/anti-S N 2′ Elimination/Cycloaddition Reaction Sequence
published pages: , ISSN: 0936-5214, DOI: 10.1055/s-0037-1610389
Synlett 2019-04-18
2018 Roly J. Armstrong, Meganathan Nandakumar, Rafael M. P. Dias, Adam Noble, Eddie L. Myers, Varinder K. Aggarwal
Enantiodivergent Synthesis of Allenes by Point-to-Axial Chirality Transfer
published pages: 8203-8208, ISSN: 1433-7851, DOI: 10.1002/anie.201804446
Angewandte Chemie International Edition 57/27 2019-04-18
2018 Venkataraman Ganesh, Adam Noble, Varinder K. Aggarwal
Chiral Aniline Synthesis via Stereospecific C(sp 3 )–C(sp 2 ) Coupling of Boronic Esters with Aryl Hydrazines
published pages: 6144-6147, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.8b02615
Organic Letters 20/19 2019-04-18
2018 Chao Shu, Riccardo S. Mega, Björn J. Andreassen, Adam Noble, Varinder K. Aggarwal
Synthesis of Functionalized Cyclopropanes from Carboxylic Acids by a Radical Addition-Polar Cyclization Cascade
published pages: 15430-15434, ISSN: 1433-7851, DOI: 10.1002/anie.201808598
Angewandte Chemie International Edition 57/47 2019-04-18
2018 Belén Rubial, Beatrice S. L. Collins, Raphael Bigler, Stefan Aichhorn, Adam Noble, Varinder Kumar Aggarwal
Enantiospecific Synthesis of ortho-Substituted 1,1-Diarylalkanes by a 1,2-Metalate Rearrangement/anti-SN2\' Elimination/Rearomatizing Allylic Suzuki-Miyaura Reaction Sequence
published pages: , ISSN: 1433-7851, DOI: 10.1002/anie.201811343
Angewandte Chemie International Edition 2019-04-18

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