Tetrahedron letters

Cascade radical cyclisations with vinylcyclopropane electrophores

G Pattenden, P Wiedenau

Index: Pattenden, Gerald; Wiedenau, Paul Tetrahedron Letters, 1997 , vol. 38, # 20 p. 3647 - 3650

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Citation Number: 27

Abstract

Treatment of the polyene iodide 3, containing a vinylcyclopropane electrophore, with tris- (trimethylsilyl) silane (TTMSS)-AIBN gave 6 and 7 (2: 1, 65%) resulting from a radical cascade 13-endo macrocyclisation followed by successive 6-exol 5-exo transannular cyclisations. In a similar manner, the iodo vinylcyclopropane 12a underwent triple cyclisation to a mixture of diastereoisomers of the oestrone analogue 14 (∼ 16%), but the ...