Atorvastatin (Lipitor) is a popular treatment for high cholesterol. See "The Importance of Hydrogen Bonding in Drug-Receptor Interactions" One synthesis of atorvastatin involves the following enolate reaction. Draw the predominant product of this reaction, which gives an overall yield of 90%. Но 1. 2 Equiv. LDA, MgBr, -78°C NH 3. H,O There are a couple of noteworthy aspects to this reaction. First, MgBr, is added to ex- change with Li and make Mg enolates. This is helpful for controlling stereochemistry. Notice that the starting material is chiral and that a single enantiomer is used. The prod- uct of this reaction is a 97:3 (94% ee) mixture of two enantiomers, not a racemic mix- ture. You don't have to be able to deduce which enantiomer is the predominant product, but be aware that being able to control the stereochemical outcome of a reaction by us- ing a single enantiomer of a chiral starting material can save time and resources in the large-scale synthesis of chiral drugs.

Atorvastatin (Lipitor) is a popular treatment for high cholesterol. See "The Importance of Hydrogen Bonding in Drug-Receptor Interactions" One synthesis of atorvastatin involves the following enolate reaction. Draw the predominant product of this reaction, which gives an overall yield of 90%. Но 1. 2 Equiv. LDA, MgBr, -78°C NH 3. H,O There are a couple of noteworthy aspects to this reaction. First, MgBr, is added to ex- change with Li and make Mg enolates. This is helpful for controlling stereochemistry. Notice that the starting material is chiral and that a single enantiomer is used. The prod- uct of this reaction is a 97:3 (94% ee) mixture of two enantiomers, not a racemic mix- ture. You don't have to be able to deduce which enantiomer is the predominant product, but be aware that being able to control the stereochemical outcome of a reaction by us- ing a single enantiomer of a chiral starting material can save time and resources in the large-scale synthesis of chiral drugs.

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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