The quest for planarizing distortions in hydrocarbons: two stereoisomeric fenestranes

Thommen, Marc; Prevot, Lionel; Eberle, Marcel K.; Bigler, Peter; Keese, Reinhart (2011). The quest for planarizing distortions in hydrocarbons: two stereoisomeric fenestranes. Tetrahedron, 67(21), pp. 3868-3873. Kidlington, UK: Elsevier Science 10.1016/j.tet.2011.03.088

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According to semiempirical calculations the planarizing distortions in the central C(C)4 substructure of fenestranes, represented as 1, can be enhanced by a variety of structural modifications. Based on these results we selected the 7-hydroxy-c,c,c,c- and c,t,c,c[]fenestranones 13 and 16 as precursors for the introduction of a bridgehead double bond. The efficient synthesis of these precursors and their chemical transformations are reported. Attempts to activate the hydroxyl group in 16 for introduction of a bridgehead double bond led to the rearrangement of the []fenestrane to a triquinacane skeleton. (C) 2011 Elsevier Ltd. All rights reserved.

Item Type:

Journal Article (Original Article)


08 Faculty of Science > Other Institutions > Emeriti, Faculty of Science
08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP)

UniBE Contributor:

Bigler, Peter and Keese, Reinhart




Elsevier Science




Factscience Import

Date Deposited:

04 Oct 2013 14:27

Last Modified:

16 Sep 2014 11:13

Publisher DOI:


Web of Science ID:


URI: (FactScience: 215552)

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