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Parallel synthesis of a desketoraloxifene analogue library via iodocyclization/palladium-catalyzed coupling.

ABSTRACT: For a future structure-activity relationship (SAR) study, a library of desketoraloxifene analogues has been prepared by parallel synthesis using iodocyclization and subsequent palladium-catalyzed coupling reactions. Points of desketoraloxifene diversification involve the two phenolic hydroxyl groups and the aliphatic amine side chain. This approach affords oxygen-bearing 3-iodobenzo[b]thiophenes 4 in excellent yields, which are easily further elaborated using a two-step approach involving Suzuki-Miyaura and Mitsunobu coupling reactions to give multimethoxy-substituted desketoraloxifene analogues 6. Various hydroxyl-substituted desketoraloxifene analogues 7 were subsequently generated by demethylation with BBr(3).

SUBMITTER: Cho CH

PROVIDER: S-EPMC3171577 | biostudies-other | 2011 Sep

REPOSITORIES: biostudies-other

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Parallel synthesis of a desketoraloxifene analogue library via iodocyclization/palladium-catalyzed coupling.

Cho Chul-Hee CH Jung Dai-Il DI Neuenswander Benjamin B Larock Richard C RC

ACS combinatorial science 20110713 5

For a future structure-activity relationship (SAR) study, a library of desketoraloxifene analogues has been prepared by parallel synthesis using iodocyclization and subsequent palladium-catalyzed coupling reactions. Points of desketoraloxifene diversification involve the two phenolic hydroxyl groups and the aliphatic amine side chain. This approach affords oxygen-bearing 3-iodobenzo[b]thiophenes 4 in excellent yields, which are easily further elaborated using a two-step approach involving Suzuki ...[more]

PMID: 21721520

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