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Org Lett. 2003 Feb 20;5(4):419-22.

Samarium(II) iodide mediated radical/polar crossover reactions of cyclobutenes. An efficient approach to the BCD ring system of the penitrems.

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1
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.

Abstract

[reaction: see text] Radical/polar crossover reactions of derivatives of 1-(2-cyclobutenyl)-2-(2-iodoaryl)ethanones with acetone promoted by samarium diiodide and HMPA provide 1-(1-hydroxy-1-methylethyl)-2,2a,4,8b-tetrahydro-1H-cyclobuta[a]naphthalen-3-one derivatives in about 50% isolated yield. This reaction shows promise for construction of the BCD ring fragment of the penitrems.

PMID:
12583733
DOI:
10.1021/ol0272491
[Indexed for MEDLINE]
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