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).

journal_name

ACS Comb Sci

authors

Cho CH,Jung DI,Neuenswander B,Larock RC

doi

10.1021/co200090p

subject

Has Abstract

pub_date

2011-09-12 00:00:00

pages

501-10

issue

5

eissn

2156-8952

issn

2156-8944

journal_volume

13

pub_type

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