Following is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose
Chapter 21, Problem 21.64(choose chapter or problem)
Following is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose struc-ture is closely related to that of tamoxifen. (a) This synthesis makes use of two blocking groups, the benzyl (Bn) group and thetetrahydropyranyl (THP) group. Draw a structural formula of each group anddescribe the experimental conditions under which it is attached and removed.(b) Discuss the chemical logic behind the use of each blocking group in this synthesis.(c) Propose a mechanism for the conversion of D to E.(d) Propose a mechanism for the conversion of F to toremifene.(e) Is toremifene chiral? If so, which of the possible stereoisomers are formed in thissynthesis?
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