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Article Dans Une Revue Synthesis: Journal of Synthetic Organic Chemistry Année : 2003

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


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.
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Dates et versions

hal-02313672 , version 1 (11-10-2019)



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⟩
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