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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.

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

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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