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The Stereoselective Introduction of the C15 OH Group on the W

Question 28

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? 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) PBr<sub>3</sub>; (2) Grubbs' catalyst,Reagent X; (3) KOC(CH<sub>3</sub>) <sub>3</sub> B) (1) PCC; (2) Ph<sub>3</sub>P=CH<sub>2</sub>; (3) Grubbs' catalyst,Reagent X C) (1) PBr<sub>3</sub>; (2) Ph<sub>3</sub>P=CH<sub>2</sub>; (3) Grubbs' catalyst,Reagent X D) (1) TsCl,pyridine; (2) Grubbs' catalyst,Reagent X; (3) KOC(CH<sub>3</sub>) <sub>3</sub>


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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