Y. Le Merrer

Total synthesis of leukotriene (+)-LTB4 from D-mannitol1

Abstract A total convergent synthesis of leukotriene (+)-LTB4 has been carried out via two enantiomerically pure α-hydroxyaldehydes,chiral key intermediates both obtained from D-mannitol and connected at a four carbon atoms interval by Wittig reactions.

Total enantiospecific syntheses of 13(S)-hydroxy 9Z, 11E-octadecadienoic (coriolic) acid and 13(S)-N-tosylamino analogue

Abstract The total syntheses of 13(S)-hydroxy 9Z, 11E-octadecadienoic (coriolic) acid and its 13(S)-N-tosylamino analogue are reported via a short, efficient, enantiospecific route from D-mannitol.

Chiral α-hydroxy- and α,β-dihydroxy- aldehydes from D-isoascorbic and L-ascorbic acids. Useful precursors for the synthesis of fatty acid metabolites.

Abstract The four possible stereoisomers of α,β-dihydroxyaldehydes, useful building blocks for the synthesis of fatty acids metabolites, are synthesized via epoxy-tetrols derived from D-isoascorbic and L-ascorbic acids. The general method we develop allows the synthesis of chiral α-hydroxyaldehydes as well.

Total synthesis of lipoxins A4 and B4 from D-isoascorbic acid

A total convergent synthesis of lipoxins A4 and B4 has been carried out via four optically pure α-hydroxy and α,β-dihydroxyaldehydes, obtained from D-isoascorbic acid as a single starting material. Connection by a six carbons unit uses Wittig-type reactions notably involving a stabilized arsonium ylide.

Syntheses of enantiomerically pure 9(S)- and 9(R)-hete from D-mannitol. Use of a malic dialdehyde equivalent.

Abstract Starting from D-mannitol, the total syntheses of methyl 9(S)- and 9(R)-hydroxy 5(Z), 7(E), 11(Z) eicosatetraenoate are described by two different ways. One route uses a diepoxide opening by an acetylide while the second one involved the transformation of a diepoxide into an equivalent of malic aldehyde, an important intermediate in the synthesis of other oxidation products of arachidonic acid. Both methods are available for the synthesis of each enantiomer.