Total synthesis confirms laetirobin as a formal Diels-Alder adduct

Simon, Oliver, Reux, Bastien, La Clair, James J. and Lear, Martin J. (2010) Total synthesis confirms laetirobin as a formal Diels-Alder adduct. Chemistry - An Asian Journal, 5 (2). pp. 342-351. ISSN 1861-4728

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Total synthesis confirms laetirobin as a formal Diels-Alder adduct

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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 bis(alkyne), 2) the practical copper(I)-mediated formation of a bis(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).

Keywords:Total synthesis, Diels-Alder, Natural product, Biomimetic synthesis, anti-tumour agents, dimerization
Subjects:F Physical Sciences > F165 Biomolecular Chemistry
F Physical Sciences > F160 Organic Chemistry
F Physical Sciences > F163 Bio-organic Chemistry
Divisions:College of Science > School of Chemistry
ID Code:17109
Deposited On:17 Apr 2015 09:56

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