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Synthesis 2010(3): 415-420
DOI: 10.1055/s-0029-1217118
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
Weitere Informationen
Received
24 September 2009
Publikationsdatum:
13. November 2009 (online)
Publikationsverlauf
Publikationsdatum:
13. November 2009 (online)
![](https://www.thieme-connect.de/media/synthesis/201003/lookinside/thumbnails/10.1055-s-0029-1217118-1.jpg)
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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References
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] .