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An enantioselective synthesis of the resorcylic acid lactone L-783,277 via addition of an acetylide anion to a tethered Weinreb amide

Lin, Andrew; Willis, Anthony; Banwell, Martin

Description

Treatment of the terminal acetylene 12, readily obtained from the previously reported acid 10, with LiHMDS resulted in a novel macrocyclization reaction to give the cycloalkyne 13. Subjection of compound 13 to hydrogenation under Lindlar-type conditions afforded the Z-configured enone 14 that could be converted into the resorcylic acid lactone 4 upon treatment with BCl3 in CH2Cl2 at -78°C.

CollectionsANU Research Publications
Date published: 2010
Type: Journal article
URI: http://hdl.handle.net/1885/57962
Source: Heterocycles
DOI: 10.3987/COM-10-S(E)67

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