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CATKERB SIGNED

Total Syntheses of Catharanthine and Keramaphidin B by an Iridium-Catalyzed Reductive Cyclization Cascade

Total Cost €

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EC-Contrib. €

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Partnership

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 CATKERB project word cloud

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

reductive    time    lewis    course    class    kb    precursor    corresponding    moiety    dixon    carry    centers    indoline    scope    perfect    p388    configured    inhibit    leukaemia    catalysts    ing    compound    cascade    mice    reaction    during    dihydropyridinones    agents    family    comprising    quaternary    catharanthine    acid    iridium    dimeric    piperidine    temperature    amine    first    usually    substituted    ic50    consists    vinblastine       methodology    iboga    28    alder    acids    dienes    syntheses    bond    cytotoxicity    pentacyclic    ml    direct    intended    substrate    keramaphidin    varying    valuable    macrocycles    cancer    group    shows    octene    subsequent    marine    establishing    azabicyclo    vincristine    cycloaddition    suitable    enantioselective    structural    total    42    alkaloids    additional    catalyzed    structurally    alkaloid    chiral    motif    belongs    cells    powerful    unbridged    catharanthus    proof    manzamine    mu    transformation    triple    treatment    natural    bridged    variant    microtubules    clinically    epidermal    rings    solvent    electron    humans    mitosis    double    feasibility    fellowship    cyclization    stereogenic    indole    diels    stage    optimization   

Project "CATKERB" data sheet

The following table provides information about the project.

Coordinator
THE CHANCELLOR, MASTERS AND SCHOLARS OF THE UNIVERSITY OF OXFORD 

Organization address
address: WELLINGTON SQUARE UNIVERSITY OFFICES
city: OXFORD
postcode: OX1 2JD
website: www.ox.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 212˙933 €
 EC max contribution 212˙933 € (100%)
 Programme 1. H2020-EU.1.3.2. (Nurturing excellence by means of cross-border and cross-sector mobility)
 Code Call H2020-MSCA-IF-2019
 Funding Scheme MSCA-IF-EF-ST
 Starting year 2020
 Duration (year-month-day) from 2020-06-01   to  2022-05-31

 Partnership

Take a look of project's partnership.

# participants  country  role  EC contrib. [€] 
1    THE CHANCELLOR, MASTERS AND SCHOLARS OF THE UNIVERSITY OF OXFORD UK (OXFORD) coordinator 212˙933.00

Map

 Project objective

During the course of this Fellowship a reductive cyclization cascade for dihydropyridinones, which consists of an iridium-catalyzed reduction to the corresponding electron-rich dienes and subsequent [42] cycloaddition (Diels-Alder reaction) will be developed. A first promising proof of concept study establishing the feasibility of this powerful transformation has already been carried out in the Dixon group; however further optimization by varying the solvent, the reaction time, the temperature or by using suitable Lewis acids is required to perfect the methodology. The additional use of chiral Lewis acid or chiral amine catalysts is also intended to develop an enantioselective variant of this method. The methodology development should then be completed by determining the substrate scope. The resulting azabicyclo[2.2.2]octene motif is an important structural component of various alkaloids. Therefore, this reaction cascade should then be used as a late stage key step in the total syntheses of the natural products catharanthine and keramaphidin B.

Catharanthine is an important member of the large class of iboga alkaloids, which usually carry as common structural feature an indole or an indoline moiety. Catharanthine can be considered as a direct precursor of the dimeric Catharanthus alkaloids vinblastine and vincristine, both of which are clinically valuable agents in the treatment of cancer due to their ability to inhibit mitosis the formation of microtubules.

The marine alkaloid keramaphidin B belongs to the manzamine family and shows cytotoxicity against P388 leukaemia cells in mice (IC50 0.28 μg/mL) and against epidermal KB cancer cells in humans (IC50 0.30 μg/mL). Structurally, keramaphidin B is a pentacyclic compound comprising two piperidine rings (one bridged and one unbridged) and two macrocycles. Furthermore, this alkaloid has two (Z)-configured and one triple-substituted double bond, as well as four stereogenic centers, one of which is quaternary.

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

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