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Abstract A method for the stereoselective construction of cis-1,2-oxazadecaline skeletons via a substrate-controlled intramolecular oxy-Michael addition of readily available tyrosine-derived hydroxylamines has been developed. The approach features an eight-step synthesis… Click to show full abstract
Abstract A method for the stereoselective construction of cis-1,2-oxazadecaline skeletons via a substrate-controlled intramolecular oxy-Michael addition of readily available tyrosine-derived hydroxylamines has been developed. The approach features an eight-step synthesis of the optically active cis-1,2-oxazadecaline enones from tyrosine esters. The described chiral pool synthetic strategy has great potential for the efficient enantioselective synthesis of natural products possessing cis-1,2-oxazadecaline frameworks, such as trichodermamides.
Journal Title: Tetrahedron Letters
Year Published: 2020
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