Merck + Co., Inc.

Marck & Co., Inc.

Kenneth M Ryan

David G Melillo

Ichiro Shinkai

Meyer Sletzinger

Thomas M Liu

Thomas R Verhoeven

Chris H Senanayake

F Edward Roberts

Ralph P Volante

David Askin

Edward F Roberts

Christ H Senanayake

Raymond J Cvetovich

A regioselective processes are disclosed for the synthesis of (1R,1S)-amino-(2S,2R)-alkanol, particularly (1R,1S)-amino-(2S,2R)-indanol.

Regiospecific processes to make cis-1-amino-2-alkanol from diol

Regiospecific processes to make CIS-1-Amino-2-Alkanol from Diol or

A regioselective process is disclosed for synthesis of 1R-amino-2S-indanol or 1S-amino-2R-indanol, wherein the stereochemical integrity of the carbon-oxygen bond at C-2 in the indene oxide starting material is retained.

Regiospecific process to make cis-1-amino-2-alkanol from epoxide

A process is described for the synthesis of diastereomeric 2-methyl-4-hydroxy-5-protected-hydroxy-hept-6-en-prolinolamides, which are useful as intermediates in the synthesis of the C.sub.10 -C.sub.18 chain of the macrolide structure for the immunosuppressant FK-506. These compounds are also useful as intermediates for preparing lactone ultraviolet radiation absorbers.

Process for synthesis of FK-506 intermediates

Disclosed is a process for the stereocontrolled total synthesis of thienamycin, which synthesis proceeds via intermediate II: ##STR1## wherein R.sup.5 and R.sup.6 are removable protecting groups.

Trans-3-carboxymethylene-4-carboxy-5-methyl-delta2-isoxazoline as

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,

Disclosed is a process for preparing the antibiotic 6-hydroxymethyl-2-(.beta.-aminoethylthio)-1-carbadethiapen-2-em-3-carboxyl ic acid (I) ##STR1## and its pharmaceutically acceptable salt and ester derivatives. An intermediate for the production of these compounds are compounds of the formula ##STR2## wherein R.sup.5 and R are readily removable protecting groups.

Process for the preparation of

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.

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

Intermediate for the preparation of thienamycin

Disclosed is a process for the stereocontrolled total synthesis of thienamycin, which synthesis proceeds via intermediate II: ##STR1## wherein R is a readily removable carboxyl protecting group; and ##STR2## is a readily removable acyl group.

Growing community of inventors

Clark, NJ, United States of America

Kenneth M Ryan