4.8 Article

Total Synthesis of Kopsone

Journal

ORGANIC LETTERS
Volume 25, Issue 15, Pages 2718-2721

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c00838

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A total synthesis of kopsone was achieved by stereoselective preparation of an acyclic aldehyde with a protected hydroxylamine moiety through Ireland-Claisen rearrangement and intramolecular cycloaddition of an eight-membered cyclic nitrone, forming the 2-azabicyclo[3.3.1]nonane skeleton.
A total synthesis of kopsone was achieved, featuring stereoselective preparation of an acyclic aldehyde having a protected hydroxylamine moiety via Ireland-Claisen rearrangement and intramolecular cycloaddition of an eight-membered cyclic nitrone to form the 2-azabicyclo[3.3.1]nonane skeleton.

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