Jean-Robert Dormoy

Alternative synthesis of the chiral atypical β-adrenergicphenylethanolaminotetraline agonist SR58611A using enantioselective hydrogenation

Abstract We have developed an alternative synthesis of the atypical β-adrenergic phenylethanolaminotetraline agonist SR58611A. Two key intermediates have been synthesised involving enantioselective hydrogenation of an aminoketone and an enamide providing the corresponding amino alcohol and amide in >96 and >98 % ee respectively.

The reaction of hexamethyl phosphoric triamide (HMPT) with phosphoryl chloride : A reexamination. Application to a novel preparation of BOP reagent for peptide coupling

Abstract The reaction of hexamethyl phosphoric triamide with phosphoryl chloride at R.T. gave actually a chlorophosphonium salt. This reaction is illustrated in a novel preparation of BOP reagent for peptide coupling in good conditions.

Synthese industrielle en serie ellipticine. I: Elaboration d'une nouvelle voie d'accès aux 6H-pyrido[4,3:b]carbazoles et analogues: A. Synthèse et étude des précurseurs.

Abstract Total synthesis of modified ellipticines 1c and 1f is described from 2-chloronicotinic acid and respectively 5-methoxy -indole and 5-azaindole in 11 to 13 steps with overall yields of 11% and 18%. A new route to 5-azaindole has also been developed. The synthetic strategy calls for frequent use of homo- and hetero aromatic metallation reactions necessiting resolution of problems associated with the presence of the pyridine ring. With respect to the numerous synthesis described in the litterature, the originality of this approach resides above all in the formation of ring C in basic medium.1 such conditions being dictated by the presence of the pyridine A ring in the case of 1f . Both synthesis have been extrapolated to produce several kilogrammes of final product. That first part deals with the preparation of the precursors.

Segment coupling in peptide synthesis—II : A simple predictive equation correlating racemization and primary structure

Abstract A predictive equation based on extrathermodynamic assumptions is proposed, that allows the prediction of the degree of epimerization in tripeptide model reactions of condensation of peptide segments as a function of the primary structure. The experimental validation of this equation is presented in the field of the 125 tripeptides containing alanine, leucine, phenylalanine, valine and isoleucine, the prediction requires 13 epimerization measurements on reference reactions. Sixteen statistically chosen predictions are checked experimentally showing a good fit in spite of the drastic basic assumptions needed to set up the equation.

Synthèse industrielle en série ellipticine. II: Elaboration d'une nouvelle voie d'accès aux 6H-pyrido[4,3:b]carbazoles et analogues : B. Obtention des structures tétracycliques

Abstract Total synthesis 1 of modified ellipticines 1c and 1f is described from 2-chloronicotinic acid and respectively 5-methoxy -indole and 5-azaindole in 11 to 13 steps with overall yields of 11% and 18%. With respect to the numerous synthesis described in the litterature, the originality of this approach resides above all in the formation of ring C in basic medium, such conditions being dictated by the presence of the pyridine A ring in the case of 1f . Both synthesis have been extrapolated to produce several kilogrammes of final product. That second part deals with the elaboration of tetracyclic structures from precursors 1 .

Le chloroformiate d'isopropenyle (ipcf) en chimie des amino-acides et des peptides - iii synthese d'esters actifs d' amino acides n-proteges

Abstract Isopropenyl chloroformate (IPCF) was used for preparation of mixed carbonates (Aryl and isopropenyl) which are very suitable reagents for active ester synthesis of amino acid derivatives ( Boc derivatives In particular).