Organic Letters 2011-06-17

Bile acid-based cage compounds with lipophilic outer shells and inner cavities.

Xinyan Bai, Charles Barnes, Robert A Pascal, Xueyi Chen, Jerry Ray Dias

Index: Org. Lett. 13(12) , 3064-7, (2011)

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Abstract

The uniquely functionalized steroid-based cyclodimers 4, cis-5, and trans-5 have been synthesized and fully characterized.The cyclodimer 5, with a cis-trans ratio of 3:1, is obtained by coupling the terminal alkenes of two 4-pentenoate groups on a cyclodimer 4 via Grubbs' intramolecular ring-closing metathesis. The crystal structure shows cis-5 to be a cagelike cyclic oligomer bridged by the flexible oct-4-enedioate link.© 2011 American Chemical Society