A new approach to desketoraloxifene analogs from oxygen-bearing 3-iodobenzo[b]thiophenes prepared via iodocyclization.
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.
Department of Chemistry, Iowa State University, Ames, Iowa 50011.
Chul-Hee
CH
Cho
Dai-Il
DI
Jung
Richard C
RC
Larock