Fusidic acid is a steroidlike microbial product that is an extremely potent antibiotic

Chapter 4, Problem 49

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Fusidic acid is a steroidlike microbial product that is an extremely potent antibiotic with a broadspectrum of biological activity. Its molecular shape is most unusual and has supplied importantclues to researchers investigating the methods by which steroids are synthesized in nature.Fusidic acid4CH3CH310CH39H5H3HOCOHOBOCCHO3 B1113 17168 14HO CH3CH3H3CH(a) Locate all the rings in fusidic acid and describe their conformations.(b) Identify all ring fusions in the molecule as having either cis or trans geometry.(c) Identify all groups attached to the rings as being either a- or b-substituents.(d) Describe in detail how this molecule differs from the typical steroid in structure and stereochemistry.(As an aid to answering these questions, the carbon atoms of the framework of themolecule have been numbered.)

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