Samarium(II) iodide mediated radical/polar crossover reactions of cyclobutenes. An efficient approach to the BCD ring system of the penitrems.
[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.
Rivkin
Alexey
A
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
Nagashima
Tadamichi
T
Curran
Dennis P
DP
D000470:Alkaloids / Q000138:chemical synthesis; D003500:Cyclization; D003503:Cyclobutanes / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis; D007454:Iodides / Q000737:chemistry; D009183:Mycotoxins / Q000138:chemical synthesis*; D012493:Samarium / Q000737:chemistry
D000470:Alkaloids; D003503:Cyclobutanes; D005609:Free Radicals; D006844:Hydrocarbons, Cyclic; D007454:Iodides; D009183:Mycotoxins; C003626:tremortin; D012493:Samarium; C409809:samarium diiodide