The Stereoselective Introduction of the C15 OH Group on the W

question 7

Multiple Choice

The stereoselective introduction of the C15 OH group on the w side chain of prostaglandins has presented a challenge for synthetic chemists.Recently, Mulzer and co-workers demonstrated a new route in which the wside chain is synthesized independently and then attached to the bicyclic counterpart.What is the appropriate sequence of reagents for the following synthesis?

• A)(1) PBr₃; (2) Grubbs' catalyst, Reagent X; (3) KOC(CH₃)₃
• B)(1) PCC; (2) Ph₃P=CH₂; (3) Grubbs' catalyst, Reagent X
• C)(1) PBr₃; (2) Ph₃P=CH₂; (3) Grubbs' catalyst, Reagent X
• D)(1) TsCl, pyridine; (2) Grubbs' catalyst, Reagent X; (3) KOC(CH₃)₃

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