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Synthesis 2010(3): 415-420  
DOI: 10.1055/s-0029-1217118
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Radical Conjugate Addition of Aryl-Tethered β-Alkoxyacrylates: Formal Synthesis of (±)-Frenolicin B and (±)-epi-Frenolicin B

Christopher D. Donner*a,b
a School of Chemistry, The University of Melbourne, Victoria 3010, Australia
b Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Victoria 3010, Australia
Fax: +61(3)93478189; e-Mail: cdonner@unimelb.edu.au;
Further Information

Publication History

Received 24 September 2009
Publication Date:
13 November 2009 (online)

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Abstract

The radical conjugate addition of aromatic-tethered O-stannyl ketyl radicals to β-alkoxyacrylates is demonstrated for the preparation of benzopyran-γ-lactone-fused tricyclic systems. This method is then applied to the stereodivergent formal synthesis of the kinase inhibitor (±)-frenolicin B and (±)-epi-frenolicin B.

Key words

radical conjugate addition - O-stannyl ketyl - frenolicin B - pyranonaphthoquinone

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16

For ease of comparison in the discussion the same numbering system is used for structures 19 and 20 in Scheme  [4] . However, the IUPAC name and numbering for 19 are given in the experimental section and depicted in Scheme  [5] .