The Stereoselective Introduction of the C15 OH Group on the W

question 20

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 w side 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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