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CATKERB SIGNED

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

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EC-Contrib. €

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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.

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

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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