Journal
ORGANIC LETTERS
Volume 23, Issue 20, Pages 7972-7975Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c02970
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Funding
- National Natural Science Foundation of China [21971249, 22171274]
- Key Research Program of the Frontier Sciences of the CAS [QYZDB-SSW-SMC026]
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The first asymmetric total synthesis of (+)-quinocarcinamide (3), an enantiomer of the natural oxidation product from antitumor antibiotic (-)-quinocarcin (1), is described, involving key steps such as iridium-catalyzed asymmetric allylic amidation of racemic alcohol 9, olefin cross-metathesis, S(N)2' reaction to forge tetrahydroisoquinoline, and stereocontrolled 1,3-dipolar cycloaddition between azomethine ylide and tert-butyl acrylate to construct the diazabicyclo[3.2.1]octane ring.
The first asymmetric total synthesis of (+)-quinocarcinamide (3), an enantiomer of the natural oxidation product from antitumor antibiotic (-)-quinocarcin (1), is described. Key steps include an iridium-catalyzed asymmetric allylic amidation of racemic alcohol 9, olefin cross-metathesis followed by a S(N)2' to forge tetrahydroisoquinoline, and stereocontrolled 1,3-dipolar cycloaddition between a facilely generated azomethine ylide and tert-butyl acrylate to construct the diazabicyclo[3.2.1]octane ring.
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