DOMDICAS

Dual Organo / Metal Desymmetrisation in Complex Alkaloid Synthesis

Coordinatore	more  Organization address address: University Offices, Wellington Square city: OXFORD postcode: OX1 2JD contact info Titolo: Ms. Nome: Gill Cognome: Wells Email: send email Telefono: +44 1865 289800 Fax: +44 1865 289801
Nazionalità Coordinatore	Non specificata
Totale costo	221˙606 €
EC contributo	221˙606 €
Programma	FP7-PEOPLE Specific programme "People" implementing the Seventh Framework Programme of the European Community for research, technological development and demonstration activities (2007 to 2013)
Code Call	FP7-PEOPLE-2013-IEF
Funding Scheme	MC-I
Anno di inizio	2015
Periodo (anno-mese-giorno)	2015-02-02   -   2017-02-01

 Partecipanti

#	participant	country	role	EC contrib. [€]
1	THE CHANCELLOR, MASTERS AND SCHOLARS OF THE UNIVERSITY OF OXFORD  Organization address address: University Offices, Wellington Square city: OXFORD postcode: OX1 2JD contact info Titolo: Ms. Nome: Gill Cognome: Wells Email: send email Telefono: +44 1865 289800 Fax: +44 1865 289801	UK (OXFORD)	coordinator	221˙606.40

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 Obiettivo del progetto (Objective)

'The combination of an organocatalyst and a metal catalyst in a single transformation provides novel reactivity and high control in the creation of new bonds. However, this approach has never been applied to the synthesis of complex natural alkaloids. The aim of DOMDICAS is the development of a novel dual-catalysed asymmetric desymmetrisation methodology and its application to the synthesis of Strychnos alkaloids leuconicines A and B. In the first stage of the proposed research, a dual catalytic system, formed by an organocatalyst and a metal catalyst, will be developed for the construction of the key morphan core of leuconicines. The transformation will be carefully studied in order to obtain optimal reactivity and stereocontrol. The methodology will then be extended to a two-component arylative/vinylative version, which will make the desymmetrisation approach more general and useful. The development of this powerful methodology will be crucial for the proposed synthesis of leuconicines A and B. In the key desymmetrisation step the morphan core of the alkaloids will be constructed and the configuration of 3 of their 4 stereocenters will be established. The proposed synthesis permits the diversification of a common late-stage intermediate to other Strychnos alkaloids. The application of this novel methodology to the total synthesis of bioactive natural products such as leuconicines will provide enough amounts of material for thorough biological studies and would also constitute a milestone for the study of structure-activity relationships. Apart from the impact of the high-quality scientific results expected from this project, DOMDICAS will strongly enhance the future career prospects of the applicant as a mature and independent researcher in the European Research Area.'