CED · Catalytic Enantioselective Dearomatisation : A New Strategy for the Synthesis of Complex Bioactive Natural Products
FP7 — People (Marie Curie Actions)
- Duration
- 2010-03-01 → 2010-06-30
- EU contribution
- €171,741
- Participants
- 1
- Scheme
- MC-IEF
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Results in brief
Catalytic Enantioselective Dearomatisation : A New Strategy for the Synthesis of Complex Bioactive Natural Products
The ability to access complex molecular frameworks from simple aromatic starting molecules makes catalytic enantioselective dearomatization (CED) a potentially powerful synthetic tool. One variation of this methodology is the 'zipper' reaction in which a linear precursor containing both the nucleophile and aldehyde is used. The aim of this project is to improve upon the initial synthesis of a model compound and investigate a 'zipper' reaction using an oxygen nucleophile in the CED process.
Data: CORDIS, © European Union
Project objective
This proposal outlines a blueprint towards the development of a new catalytic strategy for chemical synthesis, wherein catalytic cascade processes are designed around the transformation of a common functional motif to a diversity of enantiopure natural product architectures, in a single step. The hypothesis behind the chemo-catalytic synthesis strategy involves the development of a catalytic enantioselective dearomatization (CED) process that directly converts flat aromatic molecules into complex asymmetric structures. The transformation involves a tandem process, comprising oxidative dearomatization and organocatalytic desymmetrization, generating highly functionalized, non-racemic architectures. The natural product targets structures of alkaloids, polyketide, steroid and terpene biosynthetic origin, and complex non-natural frameworks that may have interesting properties, as the basis for novel small-molecule libraries with untapped biological properties. The programme of research will focus on the exploitation and the development of the cascade ‘zipper-reaction’ concept, CED, wherein simple, linear molecules can be directly converted to complex enantiopure architectures that closely resemble the structures of bioactive natural products. The proposal will have four parts over the two-year period of the proposed Fellowship : the method development for the CED cascade process, the total synthesis of morphine and the development of novel scaffolds for drug discovery. The research outlined in this proposal is a representative part of a 'grand challenge' programme to provide a chemo-catalysis blueprint for synthesis that is inspired by the efficacy of biosynthesis.
Original text from CORDIS.
Participants
- THE CHANCELLOR MASTERS AND SCHOLARS OF THE UNIVERSITY OF CAMBRIDGE · CAMBRIDGECoordinatorUnited Kingdom
Links
Data: CORDIS, © European Union