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GRITAP

A General Strategy for the Iterative Assembly of Complex 1,3-Polyol Motifs

Total Cost €

0

EC-Contrib. €

0

Partnership

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 GRITAP project word cloud

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

interconversions    active    chain    conversion    ester    carbon    substituents    ubiquitous    extension    whilst    contrast    purifications    lithiation    chemical    strategy    though    polyboronic    dialled    synthetic    chains    stereochemistry    iterative    apparent    attractive    subsequent    borylation    route    reveals    complete    archetypical    group    bahamaolide    synthesis    rare    tactic    methyl    contiguous    molecule    relative    hugely    pronounced    efficient    macrocyclic    reagent    molecules    homologation    potent    herein    promises    line    biomolecules    biological    boron    oxidation    nature    preparing    bearing    essentially    polyketide    natural    always    esters    functional    total    catalytic    polyol    stereocontrolled    immediately    outline    uses    small    extensively    strategies    hydroxyl    repeat    assembly    units    an    polyene    antifungal    class    enabled    polyols    requiring    absolute    biologically    diboration    boronic    reported    compounds    hinges    desired    pot   

Project "GRITAP" 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]
 Total cost 183˙454 €
 EC max contribution 183˙454 € (100%)
 Programme 1. H2020-EU.1.3.2. (Nurturing excellence by means of cross-border and cross-sector mobility)
 Code Call H2020-MSCA-IF-2016
 Funding Scheme MSCA-IF-EF-ST
 Starting year 2017
 Duration (year-month-day) from 2017-07-01   to  2019-06-30

 Partnership

Take a look of project's partnership.

# participants  country  role  EC contrib. [€] 
1    UNIVERSITY OF BRISTOL UK (BRISTOL) coordinator 183˙454.00

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 Project objective

An attractive approach to preparing molecules with common repeat units is iterative synthesis, an approach that is extensively used by Nature in the synthesis of large biomolecules. Nature also uses this tactic for small-molecule synthesis even though common repeat units are not always immediately apparent, the archetypical example being polyketide synthesis. In contrast, iterative strategies in chemical synthesis are often much less efficient requiring several functional-group interconversions and purifications between chain-extension steps. We recently reported an “Assembly Line Synthesis” method for the iterative, reagent-controlled homologation (chain extension) of a boronic ester. This process enabled the conversion of a simple boronic ester into a molecule bearing 10 contiguous methyl substituents in an effectively “one-pot” process. Whilst these methyl-rich carbon chains are rare in natural products, hydroxyl-rich carbon chains (1,3-polyols) are ubiquitous and often show pronounced and useful biological activity. It would therefore be very useful if this or a related strategy could be applied to the fully stereocontrolled synthesis of 1,3-polyols. Herein, we outline a general strategy for the synthesis of 1,3-polyols that hinges on the merging of two well-established methodologies: lithiation–borylation and catalytic diboration. We expect to achieve complete control over both relative and absolute stereochemistry in the iterative synthesis of 1,3-polyboronic esters, enabling stereochemistry to be essentially dialled-in. Subsequent oxidation of the boron esters reveals the desired 1,3-related polyol. The strategy will be applied to the total synthesis of one of the most complex polyols known, bahamaolide A, a macrocyclic polyol–polyene natural product with potent antifungal properties. This strategy promises to be the most efficient synthetic route to these highly biologically active and hugely important class of compounds.

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The information about "GRITAP" are provided by the European Opendata Portal: CORDIS opendata.

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