Abstract
Aldolase antibody 38C2 (Aldrich no. 47,995-0) catalyzes the aldol reaction between hydroxyacetone and aldehyde 7 to give dihydroxyketone 8a in an enantiomeric excess (ee) > 99 %. This reaction has been performed on a semi- preparative scale to give the product in 55 % yield (eea 98 %). Aldol 8a can be converted to hydroxybrevicomins ent-5 and ent-6 by reduction and acid-catalyzed cyclization. Antibody 38C2 also catalyzes the retro-aldol reaction of racemic syn-8. After 52 % conversion, the enantiomeric product (8b) is obtained in > 99 % ee .B y using either antibody-catalyzed aldol or retro-aldol reactions, both aldol enantiomers can be prepared with a single antibody catalyst. This methodology has been applied in highly enantioselective total syntheses of ten brevicomins.
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