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- Title
Base-Induced Decarboxylation of Polyunsaturated α-Cyano Acids Derived from Malonic Acid: Synthesis of Sesquiterpene Nitriles and Aldehydes with β-, φ-, and ψ-End Groups.
- Authors
Dufossé, Laurent; Cartier, Dominique; Valla, Benoist; Fouillaud, Mireille; Labia, Roger; Valla, Alain
- Abstract
Catalytic base-induced decarboxylation of polyunsaturated α-cyano- β-methyl acids derived from malonic acid led to the corresponding nitriles 3 ( Schemes 2 and 3), 6 ( Scheme 5), and 9 ( Scheme 6). This decarboxylation occurred with previous deconjugation of the α, β-alkene moiety of the α-cyano- β-methyl acid, leading to an α-cyano- β-methylene propanoic acid which was easily decarboxylated (see Scheme 2). β-Methylene intermediates, in some cases, could be isolated; mechanistic pathways are proposed. The nitriles 3, 6, and 9 were reduced to the sesquiterpene aldehydes 4 ( β-end group), 7 ( φ-end group), and 10 ( ψ-end group), respectively.
- Subjects
DECARBOXYLATION; MALONIC acid; CARBOXYLIC acids; DICARBOXYLIC acids; SESQUITERPENES; ALDEHYDES
- Publication
Helvetica Chimica Acta, 2013, Vol 96, Issue 2, p259
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.201200162