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

Alexey Rivkin; Tadamichi Nagashima; Dennis P Curran

doi:10.1021/ol0272491

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

Org Lett. 2003 Feb 20;5(4):419-22. doi: 10.1021/ol0272491.

Authors

Alexey Rivkin¹, Tadamichi Nagashima, Dennis P Curran

Affiliation

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

PMID: 12583733
DOI: 10.1021/ol0272491

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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Alkaloids / chemical synthesis
Cyclization
Cyclobutanes / chemistry
Free Radicals / chemistry
Hydrocarbons, Cyclic / chemical synthesis
Iodides / chemistry
Mycotoxins / chemical synthesis*
Samarium / chemistry

Substances

Alkaloids
Cyclobutanes
Free Radicals
Hydrocarbons, Cyclic
Iodides
Mycotoxins
tremortin
Samarium
samarium diiodide