Jean-Louis Montero

A convenient synthesis of peracetylated glycosyl halides using bismuth(III) halides as catalysts

Abstract A new halogenation procedure for peracetylated glycopyranosides is reported, using bismuth(III) halides and halogenosilanes under very mild conditions.

Homologation of carboxylic acids by arndt-eistert reaction under ultrasonic waves

Abstract The use of ultrasonic activation in the Arndt-Eistert reaction leads rapidly, in good yields, to the expected compounds at room temperature.

A SIMPLE, GENERAL AND EFFICIENT METHOD FOR O AND N-RETINOYLATION. APPLICATION TO THE SYNTHESIS OF 2-RETINOYL-LECITHIN.

Abstract The synthesis of the new l-stearoyl-2-retinoyl-glycero-3-phosphorylcholine by coupling of retinoic acid and lysolecithin with DCC-DMAP (1.2 eq.) is reported. This method is applied to O and N-retinoylation of uncharged organic substrates such as aliphatic alcohols, free hydroxyl anomeric sugars, aromatic amines and C-protected α-aminoacids.

Sequential radical cyclization of β-functionalized allyl bromomethyldimethylsilyl ethers. Application to the regio- and stereo-specific synthesis of an isoprostanoid precursor

The behaviour of allyl bromomethyldimethylsilyl ethers β-substituted by various radical trapping functions (aldehyde, nitrile or acetylenic) is studied in tandem radical cyclizations. Only homopropargylic ethers (but-3-ynylic ethers) lead to the formation of cyclic compounds via a 5-exo-trig, 5-exo-dig or 5-exo-trig, 6-endo-dig mode. The influence of the TMS group located on the acetylenic moiety is shown to be determinant for the regio- and stereo-specific C5 ring closure (5-exo-dig mode).

SYNTHESIS OF PHOSPHONATE ANALOGUES OF RETINYL PHOSPHATE

Abstract The access to phosphonates isosteres or homologues of natural retinylphosphate-target was developed starting from carbonylated terpenes, through Abramov and Wittig-Horner reactions.