Heteroaromatic Synthesis via Olefin Cross-Metathesis: Entry to Polysubstituted Pyridines

Timothy J. Donohoe, Jose A. Basutto, John F. Bower, Akshat Rathi

Research output: Contribution to journalArticle (Academic Journal)peer-review

65 Citations (Scopus)

Abstract

The olefin cross-metathesis reaction provides a rapid and efficient method for the synthesis of alpha,beta-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.

Original languageEnglish
Pages (from-to)1036-1039
Number of pages4
JournalOrganic Letters
Volume13
Issue number5
DOIs
Publication statusPublished - 4 Mar 2011

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