Danielle Jaggi

Diastereoselectivity in the directed aldol condensation of 2-trimethylsiloxyfuran with aldehydes. A stereodivergent route to threo and erythro δ-hydroxy-γ-lactones

Abstract Threo and erythro -δ-hydroxy-α,β-unsaturated γ-lactones are obtained with useful diastereoselection by condensing 2-trimethylsiloxyfuran and aldehydes by varying the reaction reaction conditions. A stereomechanistic rationale is presented together with a practical two-step synthesis of the threo and erythro 5-hydroxy-4-decanolides (L factors).

The synthesis of (±)-cavernosine

Abstract The title compound and its epimer were synthesized in three and two steps from dihydro-β-ionone and 2-trimethylsiloxyfuran in 38 and 63% overall yields respectively. Their relative configurations were confirmed by X-ray of an intermediate.

Total synthesis of bromobeckerelide

Abstract The first synthesis of (±)-bromobeckerelide has been accomplished in five steps from 5-methylfurfural by exploiting the regiospecific aldolization of a dialkylboron 2-furanolate.

A short, stereodivergent synthesis of the racemic erythro and threo diastereomers of 6-acetoxy-5-hexadecanolide, a mosquito oviposition attractant pheromone

Abstract A versatile 3-step synthesis of the title lactones has been accomplished by the stereocontrolled addition of n -decylmetallic reagents to acrolein dimer.

Regioselective aldol condensations of boron and tin furanolates with aldehydes: an improved synthesis of 2-(1′-hydroxyalkyl)butenolides

Boron and tin(II) 2-furanolates generated in situ from 2-(5H)-furanone and α-angelica lactone undergo regioselective aldolization with aldehydes to furnish the corresponding 2-(1′-hydroxyalkyl)butenolides in good yields; a new formal synthesis of (±)-litsenolide C1 and (±)-dihydromahubanolide is described.