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Enantioselective Total Synthesis of Some Brevicomins Using Aldolase Antibody 38C2

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Citation

List, B., Shabat, D., Barbas III, C. F., & Lerner, R. A. (1998). Enantioselective Total Synthesis of Some Brevicomins Using Aldolase Antibody 38C2. Chemistry – A European Journal, 4(5), 881-885. doi:10.1002/(SICI)1521-3765(19980515)4:5<881:AID-CHEM881>3.0.CO;2-%23.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-A4F9-A
Abstract
Antibody catalysis has been used for the first time in a very efficient and highly enantioselective synthesis of natural products. Aldolase antibody 38C2 (Aldrich no. 47,995‐0) catalyzes the aldol reaction between α‐hydroxylated ketones and aldehydes to give syn‐α,β‐dihydroxy ketones with ee values>99% (see below). Since 38C2 also catalyzes the retro‐aldol reaction, it is possible to prepare the other enantiomers by kinetic resolution. This has been applied in total syntheses of ten brevicomins.