Heteroaromatic synthesis via olefin cross-metathesis: entry to polysubstituted pyridines.
The olefin cross-metathesis reaction provides a rapid and efficient method for the synthesis of α,β-unsaturated 1,5-dicarbonyl derivatives which then serve as effective precursors to mono-tetrasubstituted pyridines. Manipulation of the key 1,5-dicarbonyl intermediate allows access to pyridines with a wide range of substitution patterns. An extension of this methodology facilitates the preparation of pyridines embedded within macrocycles, as exemplified by an efficient synthesis of (R)-(+)-muscopyridine. High levels of regiocontrol, short reaction sequences, and facile substituent variation are all notable aspects of this methodology.
Department of Chemistry, University of Oxford, Oxford, UK. timothy.donohoe@chem.ox.ac.uk
Timothy J
TJ
Donohoe
José A
JA
Basutto
John F
JF
Bower
Akshat
A
Rathi
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D011725:Pyridines; C071830:muscopyridine