Cholesterol surrogates incorporating a benzophenone as part of the sterol tetracycle.

J Org Chem

Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, USA.

Published: August 2006

Photoactivatable analogues 4-6 of cholesterol (1), having their cross-linking site in the ring D sterol region, have been synthesized starting from bromotetralone 14 via enantioselective Robinson annulation to enone 13 and Suzuki carbonylative coupling to the appropriate phenylboronic acid. Each of 4-6 was shown to substitute successfully for 1 in an assay of apo A-I-induced cellular cholesterol efflux, indicating that these analogues equilibrated with 1 in all major cellular pools.

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http://dx.doi.org/10.1021/jo060480yDOI Listing

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