Aldolase-Catalyzed Synthesis of Conformationally Constrained Iminocyclitols: Preparation of Polyhydroxylated Benzopyrrolizidines and Cyclohexapyrrolizidines
journal contributionposted on 07.03.2014 by Pedro Laborda, Francisco J. Sayago, Carlos Cativiela, Teodor Parella, Jesús Joglar, Pere Clapés
Any type of content formally published in an academic journal, usually following a peer-review process.
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.