A finding that opened a route to b-blockers was the discovery that b-blocking activ-ity
Chapter 21, Problem 21.58(choose chapter or problem)
A finding that opened a route to b-blockers was the discovery that b-blocking activ-ity is retained if an oxygen atom is interposed between the aromatic ring and the sidechain. To see this difference, compare the structures of labetalol ( 22.57) andpropranolol. Thus, alkylation of phenoxide ions can be used as a way to introduce thisside chain. The first of this new class of drugs was propranolol. (a) Show how propanolol can be synthesized from 1-naphthol, epichlorohydrin(Section 11.10), and isopropylamine.(b) Is propranolol chiral? If so, which of the possible stereoisomers are formed in thissynthesis?
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