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Volume 82, Issue 1
Received, 24th June, 2010, Accepted, 21st July, 2010, Published online, 22nd July, 2010. |
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| An Enantioselective Synthesis of the Resorcyclic 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 |
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Abstract
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. |
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Graphical Abstract
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| Corresponding author; email: mgb@rsc.anu.edu.au |
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