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The SmI2-H2O reagent system mediates challenging 5-exo/6-exo lactone radical cascade cyclisations that deliver carbo[5.4.0]bicyclic motifs in a diastereoselective, one-pot process that establish two new carbocyclic rings and four stereocentres.

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On the Stereoselectivities of Some Hindered Diels-Alder Reactions. -Both inter-and intramolecular Diels-Alder reactions of dienyl methyl fumarate [e.g. (I) and (III)] give cis-fused lactones with a methyl bearing quaternary centre as the major products because of the influence of the methyl substituent. A similar reaction of pyrrolinone (XII) gives mainly endo-product with two adjacent quaternary centres. -(HOATHER, H. A.; RAFTERY, J.; YALAVAC, I.; THOMAS*, E. J.; Tetrahedron 71 (2015) 24, 4124-4131, http://dx.doi.org/10.1016/j.tet.2015.04.101 ; Sch. Chem., Univ. Manchester, Manchester M13 9PL, UK; Eng.) -L. Grundl 39-097

SmI 2-H2O-Mediated 5-exo/6-exo Lactone Radical Cyclization Cascades. -The title reaction gives the products as single diastereoisomers. The obtained [5.4.0]-carbocycles with two new carbocyclic rings are important natural product targets. -(YALAVAC, I.; LYONS, S. E.; WEBB, M. R.; PROCTER*, D. J.; Chem. Commun. (Cambridge) 50 (2014) 85, 12863-12866, http://dx.doi.org/10.1039/C4CC05404K ; Sch. Chem., Univ. Manchester, Manchester M13 9PL, UK; Eng.) -B. Bergmann 11-113