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.

Enzymes in organic synthesis. 32. Stereospecific horse liver alcohol dehydrogenase-catalyzed oxidations of exo- and endo-oxabicyclic meso diols

1984 ◽  
Vol 62 (11) ◽  
pp. 2578-2582 ◽  
Author(s):  
J. Bryan Jones ◽  
Christopher J. Francis
Keyword(s):  
Alcohol Dehydrogenase ◽  
Organic Synthesis ◽  
Horse Liver Alcohol Dehydrogenase ◽  
Preparative Scale ◽  
Enantiomerically Pure ◽  
Liver Alcohol Dehydrogenase ◽  
Horse Liver ◽  
One Step ◽  
Catalyzed Oxidation ◽  
Enzymes In Organic Synthesis

Preparative-scale horse liver alcohol dehydrogenase-catalyzed oxidation of mesoexo- and endo-7-oxabicyclo[2.2.1]heptane diols provides a direct one-step route to enantiomerically pure chiral γ-lactones of the oxabicyclic series.

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.

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