Danielle Jaggi | Researchain

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Tetrahedron Letters | 1987

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

Charles W. Jefford; Danielle Jaggi; John Boukouvalas

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).

Tetrahedron Letters | 1987

The synthesis of (±)-cavernosine

Charles W. Jefford; Danielle Jaggi; Gérald Bernardinelli; John Boukouvalas

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.

Tetrahedron Letters | 1989

Total synthesis of bromobeckerelide

Charles W. Jefford; Danielle Jaggi; John Boukouvalas

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.

Tetrahedron Letters | 1986

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

Charles W. Jefford; Danielle Jaggi; John Boukouvalas

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

Journal of The Chemical Society, Chemical Communications | 1988

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

Charles W. Jefford; Danielle Jaggi; John Boukouvalas

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.

Helvetica Chimica Acta | 1995

Synthesis, Structure, and Antimalarial Activity of Some Enantiomerically Pure, cis-fused cyclopenteno-1,2,4-trioxanes

Charles W. Jefford; Shigeo Kohmoto; Danielle Jaggi; Géza Timári; Jean-Claude Rossier; Manyck Rudaz; Olivier Barbuzzi; David Gerard; Ulrich Burger; Philippe Kamalaprija; Jiri Mareda; Gérald Bernardinelli; Ignacio Manzanares; Craig J. Canfield; Suzanne L. Feck; Brain L. Robinson; W. Peters

Journal of the American Chemical Society | 1983

Reaction of bicyclic endo peroxides with carbonyl compounds. A new approach to 1,2,4-trioxanes

Charles W. Jefford; Danielle Jaggi; John Boukouvalas; Shigeo Kohmoto

Helvetica Chimica Acta | 1984

The Reaction of Singlet Oxygen with 1,3-Dimethylindole in the Presence of Aldehydes. Formation of 1,2,4-Trioxanes†

Charles W. Jefford; Danielle Jaggi; John Boukouvalas; Shigeo Kohmoto; Gérald Bernardinelli

Helvetica Chimica Acta | 1984

A New Approach to 1,2,4‐Trioxanes form Cyclic Allylic Hydroperoxides

Charles W. Jefford; Danielle Jaggi; Shigeo Kohmoto; John Boukouvalas; Gérald Bernardinelli

Helvetica Chimica Acta | 1986

Intramolecular Oxygen Transfer on the Ozonolysis of a Diphenylcyclopentene Derivative

Charles W. Jefford; John Boukouvalas; Danielle Jaggi; Shigeo Kohmoto; Gérald Bernardinelli

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