Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5220120 | Tetrahedron | 2011 | 6 Pages |
Abstract
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[4.5.5.5]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 [4.5.5.5]fenestrane to a triquinacane skeleton.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Marc Thommen, Lionel Prevot, Marcel K. Eberle, Peter Bigler, Reinhart Keese,