Enzymes in organic synthesis. 36. Synthesis of optically active civet constituent from an enzyme-generated chiral synthon

1987 ◽  
Vol 65 (4) ◽  
pp. 704-707 ◽  
Author(s):  
J. Bryan Jones ◽  
R. Scott Hinks
Keyword(s):  
Acetic Acid ◽  
Organic Synthesis ◽  
Pancreatic Lipase ◽  
Optically Active ◽  
Starting Material ◽  
Porcine Pancreatic Lipase ◽  
Hydrolysis Of ◽  
Enzymes In Organic Synthesis ◽  
Chiral Synthon

A synthesis of the civet constituent, (+)-(S,S)-(cis-6-methyltetrahydropyran-2-yl)acetic acid, is described, in which the key stereochemistry of the chiral starting material is set by an enantiotopically selective, porcine pancreatic lipase-catalyzed, hydrolysis of a meso diester.

Recent Studies on the Application of Enzymes in the Synthesis of Polyesters

1990 ◽  
Vol 218 ◽  
Author(s):  
Cary J. Morrow ◽  
Eugenia M. Brazwell ◽  
Dianela Filos ◽  
Juanita Mercure ◽  
Rosemary Romero ◽  
...  
Keyword(s):  
Molecular Weight ◽  
Ambient Temperature ◽  
Organic Solvents ◽  
Pancreatic Lipase ◽  
Bound Water ◽  
Optically Active ◽  
Porcine Pancreatic Lipase ◽  
Dibenzyl Ether ◽  
High Boiling Solvent ◽  
Hydrolysis Of

AbstractEnzyme-catalyzed preparation of polymers offers several potentially valuable advantages over the usual polymerization procedures. This paper summarizes our successful use of lipase-catalyzed polycondensations to prepare both a series of achiral [AA-BB]x polyesters from bis(2,2,2- trichloroethyl) alkanedioates and diols and of an optically active, epoxy-substituted polyester having a stereochemical purity estimated to be greater than 96%, from racemic bis(2,2,2-trichloroethyl) trans-3,4-epoxyhexanedioate and 1,4-butanediol. All of the reactions were carried out at ambient temperature in anhydrous, low to intermediate polarity, organic solvents such as ether, THF, 2-ethoxyethyl ether, dibenzyl ether, o-dichlorobenzene, or methylene choride, using porcine pancreatic lipase (PPL) as the catalyst. The molecular weight achieved by the polycondensation is limited by accumulation of the trihaloethanol that forms as the reaction progresses, probably because it frees enzyme-bound water permitting hydrolysis of the polymer to occur. This problem has been alleviated by using a high boiling solvent and removing the alcohol by placing the re'action mixture under vacuum.

Selective Acetate Hydrolysis of Diastereomers with Porcine Pancreatic lipase (PPL) as an Access to Useful Chiral Building Blocks

1992 ◽  
Vol 1992 (11) ◽  
pp. 1131-1135 ◽  
Author(s):  
Johann Mulzer ◽  
Stefan Greifenberg ◽  
Anne Beckstett ◽  
Matthias Gottwald
Keyword(s):  
Pancreatic Lipase ◽  
Building Blocks ◽  
Porcine Pancreatic Lipase ◽  
Hydrolysis Of

Enzymes in organic synthesis. 26.Synthesis of enantiomerically pure grandisol from an enzyme-generated chiral synthon

1982 ◽  
Vol 60 (15) ◽  
pp. 2007-2011 ◽  
Author(s):  
J. Bryan Jones ◽  
Mark A. W. Finch ◽  
Ignac J. Jakovac
Keyword(s):  
Organic Synthesis ◽  
Pure Material ◽  
Enantiomerically Pure ◽  
Optically Pure ◽  
Enzymes In Organic Synthesis ◽  
Chiral Synthon

The synthesis of enantiomerically pure (+)-grandisol has been achieved from an enzymically generated chiral synthon. The synthesis is an efficient one, the yield of optically pure material being 12% up to the penultimate step and 3% overall.

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