Merck + Co., Inc.

Meyer Sletzinger

Thomas M Liu

Sandor Karady

Ichiro Shinkai

Burton G Christensen

Lovji D Cama

David G Melillo

Kenneth M Ryan

Thomas R Verhoeven

Ralph P Volante

James M McNamara

Edward J Grabowski

Edward G Corley

Robert A Reamer

Erwin F Schoenewaldt

Ulf-H Dolling

Leonard M Weinstock

Seemon H Pines

George G Hazen

Raymond J Cvetovich

Theresa Y Cheng

A stereoselective process for the preparation of antihypercholesterolemic agents of the HMG-CoA reductase inhibitor type comprises treatment of an intermediate .beta.-hydroxyketone with a trialkylborane and sodium borohydride at low temperatures.

Process for preparing HMG-CoA reductase inhibitors with a

A novel process for the preparation of intermediates in the totally synthetic antihypercholesterolemic agents, 6-[2-[1,1'-biphenyl]-2-yl-ethenyl] pyranones, involving a highly efficient nickel catalyzed aryl cross-coupling reaction is disclosed.

Process for the preparation of biphenyl intermediates

This invention relates to a novel process for the preparation of 3-hydroxy-3-methylglutarylcoenzyme A (HMG-CoA) reductase inhibitors which contain a 4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one moiety, such as compactin and mevinolin, by utilizing an alkyl 4-cyano-3(R)-hydroxybutanoate as a chiral synthon for the stereospecific introduction of the 4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one moiety.

Process for the preparation of HMG-CoA reductase inhibitors and

The compound 6(R)-[2-8(S)(2,2-dimethylbutyryloxy)-2(S),6(S)-dimethyl-1,2,3,4,4a(S),5,6, 7,8,8a(S)-decahydronaphthyl-1(S)ethyl]-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-p yran-2-one is prepared in two steps from mevinolin and comprise reduction of the two double bonds and C-methylation of the 8(S)-(2-methylbutyryloxy) group to form the 2,2-dimethylbutyryloxy group. The two steps can be performed in either order.

Processes for preparing

This invention relates to a novel process for the preparation of 3-hydroxy-3-methylglutarylcoenzyme A (HMG-CoA) reductase inhibitors which contain a 4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one moiety, such as compactin and mevinolin, by utilizing an alkyl 4-halo-3(S)-hydroxybutanoate as a chiral synthon for the stereospecific introduction of the 4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one moiety.

Process for the preparation of HMG-CoA reductase inhibitors

Disclosed is a process for the stereocontrolled total synthesis of thienamycin via intermediates II and IIa: wherein R is a readily removable carboxyl protecting group.

Synthesis of thienamycin via (3SR, 4RS)-3-[1

Disclosed is a process for the stereocontrolled total synthesis of thienamycin via intermediates II and IIa: ##STR1## wherein R is a readily removable carboxyl protecting group.

1-Hydroxyethyl-2-amino pentanedioic acid derivatives

Disclosed is a process for the stereocontrolled total synthesis of thienamycin from acetone dicarboxylate via intermediate II: ##STR1## wherein R is a readily removable carboxyl protecting group.

Hydroxy amino dicarboxylic acids and esters

Disclosed is a process for the stereocontrolled total synthesis of thienamycin, which synthesis proceeds via intermediate II: ##STR1## wherein R.sup.3 is a readily removable carboxyl protecting group.

Synthesis of thienamycin via esters of (3SR,

Methylvanillyl ketone is prepared from a 'through process' involving oxidation of isoeugenol followed by subsequent acidic hydrolysis.

Process for preparing methylvanillyl ketone from isoeugenol

Disclosed is a process for preparing (2S)-tetrahydro-2.alpha.-methyl-6-oxo-4.beta.-amino-2H-pyran-3.alpha.-carb oxylic acid (I) which is useful in the synthesis of thienamycin. The process proceeds via a stereospecific reduction of the 2-acetyl-3-(R)-.alpha.-methylbenzylamino-2-pentenedioic acid diester (II). ##STR1## wherein R is, .alpha.-methylbenzyl, and R.sup.1 is lower alkyl having 1-6 carbon atoms or arylalkyl such as benzyl.

Process for the preparation of

Intermediate for synthesis of thienamycin via (3SR, 4RS)-3-[1

Intermediate for the preparation of thienamycin

Process and intermediate products useful in the preparation of cephalosporin compounds having a substituent at the 7-position in place of hydrogen are provided. The new cephalosporin compounds are active against various gram-negative and gram-positive organisms.

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North Plainfield, NJ, United States of America

Meyer Sletzinger