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Synthesis of ( S )‐Propranolol by Chemicoenzymatic Approach
Author(s) -
Wang YiFong,
Kou HwangShang,
Lee Becky,
Hwang LihYueh
Publication year - 1986
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.198600025
Subject(s) - chemistry , propranolol , hydrolysis , optically active , medicinal chemistry , propanol , absolute configuration , blocking (statistics) , stereochemistry , organic chemistry , medicine , statistics , mathematics , methanol
( S )‐Propranolol, [1‐isopropylamino‐3‐(1‐naphthoxy)‐2‐propanol], which possesses important β‐adrenergic blocking activity, has been synthesized by a chemicoenzymatic approach. The 2 S ‐absolute configuration was created by the enzyme‐mediated asymmetric hydrolysis of the (±)‐2‐acetoxy‐1‐chloro‐3‐(1‐naphthoxy)‐2‐naphthoxy)‐2‐propanol. The enzymatically produced chiral intermediate was then chemically converted to optically pure ( S )‐propranolol.