Please use this identifier to cite or link to this item: https://doi.org/10.1002/asia.200900306
Title: Total synthesis confirms laetirobin as a formal diels-alder adduct
Authors: Simon, O.
Reux, B. 
La Clair, J.J.
Lear, M.J. 
Keywords: Antitumor agents
Biomimetic synthesis
Cycloaddition
Dimerization
Total synthesis
Issue Date: 1-Feb-2010
Citation: Simon, O., Reux, B., La Clair, J.J., Lear, M.J. (2010-02-01). Total synthesis confirms laetirobin as a formal diels-alder adduct. Chemistry - An Asian Journal 5 (2) : 342-351. ScholarBank@NUS Repository. https://doi.org/10.1002/asia.200900306
Abstract: Laetirobin, isolated from a parasitic fungus host-plant relationship, was synthesized in six practical steps with an overall yield of 12% from commercially available 2,4-dihydroxyacetophenone. Because the product is a pseudosymmetric tetramer of benzo[b]-furans, each step of the synthesis was designed to involve tandem operations. Highlights include: 1) the double Sonogashira reaction of a bisACHTUNGTRENUNG(alkyne), 2) the practical copper(I)-mediated formation of a bisACHTUNGTRENUNG(benzo[b]furan), and 3) the biomimetic [4+2] dimerization and unexpected cationic [5+2] annulation of gem-diaryl alkene precursors. Preliminary structure-activity relationship data between the isomeric [4+2] and [5+2] tetramers revealed only the natural product to possess promising anticancer potential. Specifically, laetirobin is capable of blocking tumor cell division (mitosis) and invoking programmed cell death (apoptosis). © 2010 Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim.
Source Title: Chemistry - An Asian Journal
URI: http://scholarbank.nus.edu.sg/handle/10635/77296
ISSN: 18614728
DOI: 10.1002/asia.200900306
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