An efficient asymmetric synthesis of an estrogen receptor modulator by sulfoxide-directed borane reduction.
نویسندگان
چکیده
An efficient asymmetric synthesis of a selective estrogen receptor modulator (SERM) that has a dihydrobenzoxathiin core structure bearing two stereogenic centers is reported. The stereogenic centers were established by an unprecedented chiral sulfoxide-directed stereospecific reduction of an alpha,beta-unsaturated sulfoxide to the saturated sulfide in one step. Studies to elucidate the mechanism for this reduction are reported. Highly efficient Cu(I)-mediated ether formation was used to install the ether side chain, and selective debenzylation conditions were developed to remove the benzyl protecting groups on the phenols.
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عنوان ژورنال:
- Proceedings of the National Academy of Sciences of the United States of America
دوره 101 16 شماره
صفحات -
تاریخ انتشار 2004