NDLI: Synthesis of Small Molecules with High Scaffold Diversity: Exploitation of Metathesis Cascades in Combination with Inter- and Intramolecular Diels–Alder Reactions

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Synthesis of Small Molecules with High Scaffold Diversity: Exploitation of Metathesis Cascades in Combination with Inter- and Intramolecular Diels–Alder Reactions

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Pedersen, Palle J. Lanyon-hogg, Thomas O'leary-steele, Catherine James, Thomas Nelson, Adam Hayes, Jerome Leach, Stuart
Description	Author Affiliation: O'Leary-Steele C ( School of Chemistry, University of Leeds, Leeds, LS2 9JT, UK.)
Abstract	Our knowledge of the biological relevance of regions of chemical space is shaped, in large part, by the synthetic accessibility of small molecules. Historically, however, chemists have explored chemical space in an exceptionally uneven and unsystematic way. We have previously demonstrated that metathesis cascade chemistry may be harnessed to yield small molecule collections with high scaffold diversity. Here, we describe the extent to which inter- and intramolecular Diels–Alder reactions, when used in conjunction with metathesis cascades, can extend the range of molecular scaffolds that are accessible. A range of metathesis substrates was prepared from combinations of two or three building blocks. Metathesis cascades were exploited to “reprogram” the molecular scaffolds. In many cases, the metathesis products were 1,3-dienes, which were potential substrates for either inter- or intramolecular Diels–Alder reactions. The synthesis and functionalisation of the products was often facilitated by fluorous tagging, for example by using a “safety-catch” linker that we have developed. It was demonstrated that, in certain cases, Diels–Alder reactions could extend the range of molecular scaffolds that may be prepared by using metathesis cascade reactions.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	31
Volume Number	16
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2010-08-16
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Heterocyclic Compounds Chemistry Molecular Structure Cyclization Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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