The Stereoselective Introduction of the C15 OH Group on the

question 20

Multiple Choice

The stereoselective introduction of the C15 OH group on the  side chain of prostaglandins has presented a challenge for synthetic chemists. Recently, Mulzer and co-workers demonstrated a new route in which the  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

---

Definitions:

Adjustments

Modifications made to improve or correct something.

Early Years

The initial stages of a person's life, typically focusing on the period from birth until entering formal education.

"Our" Money

A concept referring to shared financial resources in a partnership or family.

Allowance for Doubtful Accounts

A contra-asset account that represents receivables that are expected to become uncollectable, used to estimate bad debts.