100348-38-7Relevant articles and documents
BIOSYNTHETIC RELATIONSHIP OF ARYLTETRALIN LACTONE LIGNANS TO DIBENZYLBUTYROLACTONE LIGNANS
Kamil, Widad M.,Dewick, Paul M.
, p. 2093 - 2102 (1986)
Key Word Index - Podophyllum hexandrum; Podophyllaceae; lignans; aryltetralin; dibenzylbutyrolactone; biosynthesis; podophyllotoxin. Feeding experiments in Podophyllum hexandrum plants have shown that the dibenzylbutyrolactone lignan yatein is a satisfactory precursor of the aryltetralin lignan podophyllotoxin.The corresponding cis isomer of yatein was also incorporated, but to a lesser extent, and probably via yatein.Podorhizol, epipodorhizol and anhydropodorhizol were not incorporated into podophyllotoxin, despite the demonstrated presence of both podorhizol and anhydropodorhizol in P. hexandrum plants.A biosynthetic sequence from yatein to podophyllotoxin via a key quinonemethide intermediate is proposed.This intermediate is probably also the precursor of both podorhizol and anhydropodorhizol.Matairesinol is proposed as the branchpoint compound to the trimethoxy and hydroxydimethoxy series of aryltetralin lignans in Podophyllum.Labelling patterns in podophyllotoxin and 4'-demethylpodophyllotoxin derived from methionine support this suggestion.
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Gensler et al.
, p. 2461,2465,2466,2467 (1972)
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Chemoenzymatic Total Synthesis of Deoxy-, epi-, and Podophyllotoxin and a Biocatalytic Kinetic Resolution of Dibenzylbutyrolactones
Lazzarotto, Mattia,Hammerer, Lucas,Hetmann, Michael,Borg, Annika,Schmermund, Luca,Steiner, Lorenz,Hartmann, Peter,Belaj, Ferdinand,Kroutil, Wolfgang,Gruber, Karl,Fuchs, Michael
, p. 8226 - 8230 (2019/05/21)
Podophyllotoxin is probably the most prominent representative of lignan natural products. Deoxy-, epi-, and podophyllotoxin, which are all precursors to frequently used chemotherapeutic agents, were prepared by a stereodivergent biotransformation and a biocatalytic kinetic resolution of the corresponding dibenzylbutyrolactones with the same 2-oxoglutarate-dependent dioxygenase. The reaction can be conducted on 2 g scale, and the enzyme allows tailoring of the initial, “natural” structure and thus transforms various non-natural derivatives. Depending on the substitution pattern, the enzyme performs an oxidative C?C bond formation by C?H activation or hydroxylation at the benzylic position prone to ring closure.
Synthesis and Computational Studies Demonstrate the Utility of an Intramolecular Styryl Diels-Alder Reaction and Di-t-butylhydroxytoluene Assisted [1,3]-Shift to Construct Anticancer dl-Deoxypodophyllotoxin
Saavedra, Diana I.,Rencher, Benjamin D.,Kwon, Doo-Hyun,Smith, Stacey J.,Ess, Daniel H.,Andrus, Merritt B.
, p. 2018 - 2026 (2018/02/23)
Deoxypodophyllotoxin is a secondary metabolite lignan possessing potent anticancer activity with potential as a precursor for known anticancer drugs, but its use is limited by scarcity from natural sources. We here report the total synthesis of racemic de
