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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