Rhone-Poulenc Rorer S.a.

Merial Limited

Adisseo France Sas

Aventis Animal Nutrition S.a.

Thierry Durand

Patrick Leon

Denis Largeau

Michael O'Brien

Matthew Powers

Jildaz Dhainaut

Gilles Oddon

Denis Pauze

Ronan Guevel

Fr&eacute;d&eacute;ric Lhermitte

Ching Tsuei

Fran&ccedil;ois Basset

The invention concerns a novel method for preparing vitamin E. More particularly, it concerns a novel method for the condensation of trimethylhydroquinone and isophytol.

Process for the preparation of vitamin E

Process for preparing and isolating 9-deoxo-9 (Z)-hydroxyiminoerythromycin A

The invention concerns a novel method for preparing vitamin E. More particularly, it concerns a novel method for the condensation of Arimethylhydroquinone and isophytol.

Method for preparing vitamin e

A method for the preparation of a lactam compound of formula ##STR1## wherein R'.sub.1 and R'.sub.1 independently are acyl or aroyl, or taken together form an optionally substituted methylene, and G.sub.1 is hydrogen or an amino protecting group, comprising oxidizing a bis O-protected 1R-2-azadihydroxybicyclo-�2.2.1!heptane compound of formula ##STR2## with about 0.1 mol % to about 1 mol % of RuO.sub.2 or hydrate thereof in the presence of about 3 equivalents of an oxidant to form the lactam compound with an enantiomeric excess of greater than or equal to about 95%.

L-tartaric acid salt of a (1R) diastereomer of a

A compound of formula ##STR1## wherein R is a group of formula ##STR2## R.sub.1 is alkyl; and Ar is optionally substituted aryl.

A method according to the invention is directed to the preparation of a 2-azadihydroxybicyclo�2.2.1!heptane compound of formula ##STR1## wherein * represents an R chirality, *' represents an S chirality, R is hydrogen or, respectively, a group of formula ##STR2## wherein R.sub.1 is alkyl and Ar is optionally substituted aryl, comprising bishydroxylating a bicyclo�2.2.1!heptene compound of formula ##STR3## wherein *, *' and R are as previously defined, in the presence of about 0.1 mol to about 5 mol % of a metal osmate compound or about 0.06 mol % to about 0.07 mol % osmium tetroxide, and an oxidizing agent capable of regenerating osmium tetroxide. The invention is also directed to the treatment of the (1R) diastereomer of the 2-azadihydroxybicyclo�2.2.1!heptane compound (I) wherein R is a group of formula II with L-tartaric acid, and the L-tartaric acid salt product thereof. Furthermore, the invention is directed to using the (1R) diastereomer of the 2-azadihydroxybicyclo�2.2.1!heptane compound in an acid facilitated acetalizing or ketalizing reaction that results in the protection of the dihydroxy moieties thereof in isopropanol. In addition, the invention is directed to oxidizing a bis O-protected derivative of the (1R) diastereomer of the 2-azadihydroxybicyclo�2.2.1!heptane compound to a corresponding lactam compound in the presence of about 0.01 mol % to about 1 mol % of RuO.sub.2 with about 3 equivalents of an oxidant to form the lactam compound with in an enantiomeric excess ('ee') of greater than or equal to about 95%.

Growing community of inventors

Ecully, France

Thierry Durand