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. 2010 Dec 15;51(50):6485-6488.
doi: 10.1016/j.tetlet.2010.09.137.

A new approach to desketoraloxifene analogs from oxygen-bearing 3-iodobenzo[b]thiophenes prepared via iodocyclization

Chul-Hee Cho  1 , Dai-Il Jung, Richard C Larock
Affiliations

A new approach to desketoraloxifene analogs from oxygen-bearing 3-iodobenzo[b]thiophenes prepared via iodocyclization

Chul-Hee Cho et al. Tetrahedron Lett. .

Abstract

A formal total synthesis of the benzothiophene selective estrogen receptor modulator (SERM) desketoraloxifene and analogs has been accomplished from alkynes bearing electron-rich aromatic rings by electrophilic cyclization using I(2). This approach affords oxygen-bearing 3-iodobenzo[b]thiophenes in excellent yields, which are easily further elaborated using a two-step approach involving Suzuki-Miyaura and Mitsunobu coupling reactions.

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Figures

Figure 1
Figure 1
Chemical structures of tamoxifen (I), 4-hydroxytamoxifen (II), toremifene (III) and representative synthetic benzothiophene SERMs [e.g. raloxifene (IV), arzoxifene (V), and desketoraloxifene (VI)] with A and B rings corresponding to tamoxifen.
Scheme 1
Scheme 1
Scheme 2
Scheme 2
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