Synthesis of the angiotensin converting enzyme inhibitor (-)-A58365A via an isomünchnone cycloaddition reaction.
[formula: see text] The angiotensin converting enzyme inhibitor (-)-A58365A (1) was synthesized by a process based on the [3 + 2]-cycloaddition reaction of a phenylsulfonyl-substituted isomünchnone intermediate. The starting material for this process was prepared from L-pyroglutamic acid and involved using a diazo-phenylsulfonyl-substituted pyrrolidine imide. Treatment of the diazoimide with Rh2(OAc)4 in the presence of methyl vinyl ketone afforded a 3-hydroxy-2-pyridone derivative which was subsequently converted to the ACE inhibitor in six additional steps.
Straub
C S
CS
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
Padwa
A
A
D000806:Angiotensin-Converting Enzyme Inhibitors / Q000138:chemical synthesis*; D003500:Cyclization; D007212:Indolizines / Q000138:chemical synthesis*; D011761:Pyrrolidonecarboxylic Acid / Q000737:chemistry; D013237:Stereoisomerism
D000806:Angiotensin-Converting Enzyme Inhibitors; D007212:Indolizines; C046684:A 58365A; D011761:Pyrrolidonecarboxylic Acid