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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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 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.

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

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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