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Communication | Special issue | Vol 82, No. 1, 2010, pp.313-318
Published online, 22nd July, 2010
DOI: 10.3987/COM-10-S(E)67
An Enantioselective Synthesis of the Resorcylic Acid Lactone L-783,277 via Addition of an Acetylide Anion to a Tethered Weinreb Amide

Andrew Lin, Anthony C. Willis, and Martin G. Banwell*

*Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia


Abstract – 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.