Q5-36E - Organic Chemistry (Mcmurry)

Question

Erythronolide B is the biological precursor of erythromycin, a broadspectrumantibiotic. How many chirality centers does erythronolide B have? Identify them.

Step-by-Step Solution

Answer

The ten chiral centers of erythronolide B are shown as follows:

 

 

Chiral centers of erythronolide B

Chiral Center

The chiral center is also known as:

• Asymmetric carbon
• Asymmetric center

 

The chiral center (represented by *)  has the “tetrahedral geometry” four sigma bonds are joining the four different groups around it, shown as follows:

Chirality center in erythronolide B

Erythronolide B is the biological precursor of erythromycin, a broadspectrum antibioticwith ten carbonhybridized and attached to four different groups; thus, erythronolide B has ten chiral centers (represented by *).

 

The ten chiral centers of erythronolide B are shown as follows:

Chiral centers of erythronolide B