The shrub ma huang (Section 5.4A) contains two biologically active
stereoisomers—ephedrine and pseudoephedrine—with two stereogenic
centers as shown in the given structure. Ephedrine is one component of
a once-popular combination drug used by body builders to increase
energy and alertness, whereas pseudoephedrine is a nasal
decongestant.
a.) Draw the structure of naturally occurring (−)-ephedrine, which has the
1R,2S configuration.
b.) Draw the structure of naturally occurring (+)-pseudoephedrine, which
has the 1S,2S configuration.
c.) How are ephedrine and pseudoephedrine related?
d.) Draw all other stereoisomers of (−)-ephedrine and (+) pseudoephedrine, and give the R,S designation for all stereogenic
centers.
e.) How is each compound drawn in part (d) related to (−)-ephedrine?
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