Hoffmann-la Roche Inc.

Roche Vitamins Inc.

Erich Widmer

Reinhard Zell

Hans G Leuenberger

Hans Johann Mayer

Walter Boguth

Teodor Lukac

Milan Soukup

Emil A Broger

Yvo Crameri

Walter Rehm

Dorothea Isler

Hans Hilpert

Alois Villiger

Marquard Imfeld

Hansjorg Grass

Roland Rich

Francedillaois Montavon

Marcel Seuret

A process for the manufacture of an optionally protected 4,8,8-trimethyl-1-oxaspiro�2.5!oct-4-en-6-ol (I) starting from protected 4-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-one (II) comprises reacting the protected compound (II) with dihalomethyllithium and, if desired, cleaving off the protecting group from the thus-obtained protected 4,8,8-trimethyl-1-oxaspiro�2.5!oct-4-en-6-ol. The dihalomethyllithium can be produced in situ by reacting a dihalomethane with a lower alkyllithium in the presence of the compound of formula II. Preferably, protected (S)-4-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-one is converted into protected (3S,6S)-4,8,8-trimethyl-1-oxaspiro�2.5!oct-4-en-6-ol in this manner. Both the starting material (II) and the end product (I) of the process in accordance with the invention are known, valuable intermediates for the manufacture of carotenoids.

Process for the C.sub.1 -homologization of protected phorenol

A process for the asymmetric hydrogenation of a compound of the formula ##STR1## wherein each R, independently, is alkyl, arylmethyl, aryl, alkoxy, arylmethoxy or aryloxy or both R's, taken together, are methylene, ethylene or 1,2-phenylene and n is 1,2 or 3, or of a salt thereof to a compound of the formula ##STR2## in the form of an (S) or (R) enantiomer, wherein R and n have the significances given above, using an optically active ruthenium-diphosphine complex as catalyst, is described. The preparation of the compounds of formula II, as well as the compounds of formula II, which form a further object of the invention, are also described.

Asymmetric hydrogenation process using ruthenium-diphosphine complexe

A pharmaceutical composition comprising at least one water insoluble crude fiber and at least one lipase inhibitor. The lipase inhibitor is present in an amount effective for treating adiposity. The lipase inhibitor is selected from lipstatin in pure form, a biomass comprising a lipase inhibitor, and tetrahydrolipstatin.

Biomass lipase inhibitor useful for treating adiposity

The use of biomasses obtained in the fermentative production of lipase inhibitors, especially lipstatin, for the preparation of foodstuffs, feedstuffs, food additives, feed additives, feed supplements, medicinal feed premixes or medicaments for oral administration, are described.

Biomasses to treat non-human animals

A process for producing cycloketones of a 5 or 6 carbon chain length through which said ketones are known intermediates for producing carotenoids.

Process for carotenoid intermediates

Compounds of the formula ##STR1## wherein n is either 0 or 1; R.sup.1 and R.sup.2 is hydrogen and the other is hydrogen, hydroxy, oxo group, a protected hydroxy or protected oxo group; R.sup.3 is hydroxy oxo group, .dbd.CH--CH.sub.2 --OH, .dbd.CH--CHO or one of the foregoing groups where the hydroxy or oxo functions are protected; R.sup.4 is --CO--OR.sup.6, --CO--R.sup.6, --CO--NR.sup.6 R.sup.7, --CO--Cl or --SO.sub.2 --R.sup.6 ; R.sup.6 is saturated or aromatic hydrocarbon; and R.sup.7 is saturated or aromatic hydrocarbon or hydrogen, are converted by cleavage of R.sup.4 OH into corresponding cycloalkenes and protecting groups, if present, are hydrolyzed. The compounds obtained are valuable intermediates in carotenoid syntheses.

Substituted alkynes useful as intermediates in the synthesis of

A novel process for the manufacture of cyclohexene derivatives which are suitable as intermediates for the manufacture of rhodoxanthin or zeaxanthin, as well as a process for the manufacture of rhodoxanthin or of zeaxanthin itself. The invention is also concerned with a novel starting material and novel intermediates in this process.

Process for the manufacture of cyclohexene derivatives

A process for the manufacture of 3-hydroxy-2,6,6,-trimethyl-2-cyclohexen-2-one, an intermediate in canthaxanthin synthesis, by isomerizing 1,1,3-trimethyl-7-oxabicyclo[4.1.0]heptan-2-one in the presence of a palladium(O) complex of an acetone derivative of the formula ##STR1## wherein R.sup.1 and R.sup.2 are aryl and R.sup.3 and R.sup.4 are hydrogen or monovalent hydrocarbon groups optionally carrying a carbonyl function, a bis-(diphenylphosphino) derivative of the formula

Process for the manufacture of 3-hydroxy-2,6,6,-trimethyl-2

A process for the manufacture of 3-hydroxy-2-cycloalken-1-one derivatives by cathodically reducing a compound of the general formula ##STR1## wherein n is the integer 0 or 1, to a compound of the formula ##STR2## wherein n has the above significance, and, if desired, further cathodically reducing the resulting compound in acidic or neutral medium to a compound of the general formula ##STR3## wherein n has the above significance.

Process for the manufacture of 3-hydroxy-2-cycloalken-1-one derivatives

Disubstituted ethanes of the formula ##STR1## wherein R.sup.2 is --R.sup.3, --OR.sup.3, --CO--R.sup.3, --CO--OR.sup.3 or O--CO--R.sup.3, R.sup.1 and R.sup.3 each are straight-chain alkyl of 1 to 12 carbon atoms and n is 1 or 2, are described. Liquid crystalline mixtures comprising Compound I as well as their use in electro-optical devices also are disclosed.

Disubstituted ethanes

A process for producing 3-(5-hydroxy-3-methyl-1,3-pentadienyl)-2,4,4-trimethyl-2-cyclohexen-1-one, an intermediate for canthaxanthin, by hydrogenation of 5-(2,6,6-trimethyl-3-oxo-cyclohexen-1-yl)-3-methyl-2-penten-4-yn-1-ol with zinc and a carboxylic acid.

Process for producing cyclohexenes

The compound 6-hydroxy-3-(5-hydroxy-3-methyl-1,3-pentadienyl)-2,4,4-trimethyl-2-cyclohe xen-1-one useful as intermediate for producing the natural coloring agent astaxanthin as well as a method for synthesizing astaxanthin from this compound and synthesizing the compound from 2-hydroxyketo isophorone.

A process for fermentatively hydrogenating and reducing ketoisophorone to produce optically active [4R,6R]-4-hydroxy-2,6,6-trimethyl-cyclohexanone useful as an intermediate in the production of optically active carotenoids and intermediates in the production of these carotenoids.

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Munchenstein, Switzerland

Erich Widmer