Tetrahedron

Helical primary structures of 1, 2-spiroannelated five-membered rings: attempted synthesis of (±)-tetraspiro [4.0. 0.0. 4.3. 3.3] heneicosane

T Widjaja, L Fitjer, K Meindl, R Herbst-Irmer

Index: Widjaja, Tien; Fitjer, Lutz; Meindl, Kathrin; Herbst-Irmer, Regine Tetrahedron, 2008 , vol. 64, # 19 p. 4304 - 4312

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Citation Number: 8

Abstract

A β-hydroxy ketone with a helical carbon skeleton of five 1, 2-spiroannelated cyclopentane rings is the main product of a Lewis acid catalyzed rearrangement of suitable sized α- hydroxy epoxides followed by an in situ equilibration via retro aldol reactions. Various attempts of a conversion to the title hydrocarbon failed.