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Aldolase-Catalyzed Synthesis of Conformationally Constrained Iminocyclitols: Preparation of Polyhydroxylated Benzopyrrolizidines and Cyclohexapyrrolizidines

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journal contribution
posted on 07.03.2014, 00:00 by Pedro Laborda, Francisco J. Sayago, Carlos Cativiela, Teodor Parella, Jesús Joglar, Pere Clapés
A straightforward chemo-enzymatic synthesis of new polyhydroxylated benzo­pyrrolizidines and cyclo­hexa­pyrrolizidines is developed. The two-step strategy consists of l-fuculose-1-phosphate aldolase variant F131A-catalyzed aldol addition of dihydroxy­acetone phosphate to rac-N-benzyl­oxycarbonyl­indoline-2-carb­aldehyde as well as (2S*,3aS*,7aS*)- and (2S*,3aR*,7aR*)-N-benzyl­oxycarbonyl­octa­hydro­indole-2-carb­aldehydes and a subsequent one-step catalytic deprotection–reductive amination.