A [4+2] Heterocycloaddition Route to (±)-9-Decanolides

Arnaud Martel (1) , Vincent Maisonneuve (2) , Eric Brown (1) , Gilles Dujardin (1)

1 UCO2M - Unité de chimie organique moléculaire et macromoléculaire
2 LdOF - Laboratoire des oxydes et fluorures

A convergent synthetic pathway for access to the functionalized (±)-9-decanolides is described, using a [4+2] bicyclic heterocycloadduct as the key intermediate. Thus, the exo adduct (±)-10 led to the hemiacetal (±)-14a via a 4-step sequence. Free radical oxidation of (±)-14a by means of iodine and iodosobenzene diacetate under UV light gave the model 9-decanolide (±)-15 in 53% yield.

Mots clés: 9-decanolides; bicyclic adducts; Diels-Alder reactions; radical reactions; macrocycles; lactones

Domaines: Chimie; Chimie organique

Arnaud Martel, Vincent Maisonneuve, Eric Brown, Gilles Dujardin. A [4+2] Heterocycloaddition Route to (±)-9-Decanolides. Synthesis: Journal of Synthetic Organic Chemistry, 2003, 2003 (04), pp.0539-0544. ⟨10.1055/s-2003-37657⟩. ⟨hal-02313672⟩