Total synthesis confirms laetirobin as a formal diels-alder adduct

Oliver Simon; Bastien Reux; James J. La Clair; Martin J. Lear

doi:10.1002/asia.200900306

Total synthesis confirms laetirobin as a formal diels-alder adduct

Oliver Simon, Bastien Reux, James J. La Clair, Martin J. Lear

SCI - Chemistry

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

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).

Original language	English
Pages (from-to)	342-351
Number of pages	10
Journal	Chemistry - An Asian Journal
Volume	5
Issue number	2
DOIs	https://doi.org/10.1002/asia.200900306
Publication status	Published - 2010 Feb 1

Keywords

Antitumor agents
Biomimetic synthesis
Cycloaddition
Dimerization
Total synthesis

ASJC Scopus subject areas

Biochemistry
Organic Chemistry

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title = "Total synthesis confirms laetirobin as a formal diels-alder adduct",

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).",

keywords = "Antitumor agents, Biomimetic synthesis, Cycloaddition, Dimerization, Total synthesis",

author = "Oliver Simon and Bastien Reux and {La Clair}, {James J.} and Lear, {Martin J.}",

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AU - Reux, Bastien

AU - La Clair, James J.

AU - Lear, Martin J.

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Y1 - 2010/2/1

N2 - 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).

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