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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.

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

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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