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

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Definitions:

Absolute Value Equation

An equation that contains an absolute value expression, representing the distance of a number from zero on the real number line.

Set Notation

A standardized method of describing or defining a set by clearly specifying its elements or the properties that its members must satisfy.

Absolute Value Inequality

An inequality that involves the absolute value of a variable expression and defines a range of solutions.

Solution

A quantity or array of quantities that solve an equation, inequality, or simultaneous equations.