Answered: NH, O OH QH CO,H CO,Et Но CO̟Et…

Introduction to General, Organic and Biochemistry

11th Edition

ISBN:9781285869759

Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Chapter21: Lipids

Section: Chapter Questions

Problem 21.62P

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Question

Draw a stepwise mechanism for the following reaction, one step in the synthesis of the cholesterol-lowering drug pitavastatin, marketed in Japan as a calcium salt under the name Livalo.

NH, O
OH
QH
CO,H
CO,Et
Но
CO̟Et
pitavastatin

Expert Solution

Step 1

Protonation of oxygen atom takes place in the presence of acid H₃O⁺

Hydrogen atom migrates to convert into enol form

Now amine react ith ketone with the elimination of water to get our final product

Step 2

enol form behaves as a nucleophile

Nucleophile attack on electrophile (ketone) given in acidic medium

Step 3

Dehydration of water takes place

Rearrange the molecule

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