Helical primary structures of 1,2-spiroannelated five-membered rings: attempted synthesis of (+/-)-tetraspiro[4.0.0.0.4.3.3.3]heneicosane

ISSN
0040-4020
Date Issued
2008
Author(s)
Widjaja, Tien
Meindl, Kathrin
DOI
10.1016/j.tet.2008.02.073
Abstract
A beta-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 alpha-hydroxy epoxides followed by an in situ equilibration via retro aldol reactions. Various attempts of a conversion to the title hydrocarbon failed. (c) 2008 Elsevier Ltd. All rights reserved.