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Aldolase-catalyzed synthesis of conformationally constrained iminocyclitols: Preparation of polyhydroxylated benzopyrrolizidines and cyclohexapyrrolizidines

AuthorsLaborda, Pedro ; Sayago, Francisco J. ; Cativiela, Carlos ; Parella, Teodor; Joglar Tamargo, Jesús ; Clapés Saborit, Pere
Issue Date2014
PublisherAmerican Chemical Society
CitationOrganic Letters 16(5): 1422-1425 (2014)
AbstractA 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. © 2014 American Chemical Society.
Identifiersdoi: 10.1021/ol5002158
issn: 1523-7060
e-issn: 1523-7052
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