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Enzymes in Organic Synthesis, 8. Synthesis of enantiomerically pure prostaglandin intermediates by enzymatic transesterification of (1S*,5R*,6R*,7R*)-(±)-7-hydroxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one

✍ Scribed by Weidner, Judith ;Theil, Fritz ;Kunath, Annamarie ;Schick, Hans

Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
271 KB
Volume
1991
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Lipase Amano PS is a suitable biocatalyst for the highly regio‐ and enantioselective transesterification of the racemic prostaglandin building block (1__S__~*~,5__R__*,6__R__*,7__R__*)‐(±)‐7‐hydroxy‐6‐hydroxymethyl‐2‐oxabicyclo[3.3.0]octan‐3‐one (rac‐1) yielding (1__S__,5__R__,6__R__,7__R__)‐(−)‐6‐acetoxymethyl‐7‐hydroxy‐2‐oxabicyclo[3.3.0]octan‐3‐one (2) and the unreacted (1__R__,5__S__,6__S__,7__S__)‐(+)‐enantiomer ent‐1.

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