Cholesterol surrogates incorporating a benzophenone as part of the sterol tetracycle |
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Authors: | Gan Yonghong Spencer Thomas A |
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Affiliation: | Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, USA. |
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Abstract: | 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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