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

Pedro Laborda, Francisco J. Sayago, Carlos Cativiela, Teodor Parella, Jesús Joglar, Pere Clapés

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    18 Citations (Scopus)

    Abstract

    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. © 2014 American Chemical Society.
    Original languageEnglish
    Pages (from-to)1422-1425
    JournalOrganic Letters
    Volume16
    Issue number5
    DOIs
    Publication statusPublished - 7 Mar 2014

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