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Catherine J. Fletcher, Dr. Katherine M. P. Wheelhouse and Prof. Varinder K. Aggarwal Stereoselective Total Synthesis of (+)-Giganin and Its C10 Epimer by Using Late-Stage Lithiation–Borylation Methodology Angewandte Chemie International Edition 52

Version of Record online: 25 JAN 2013 | DOI: 10.1002/anie.201208403

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The first total synthesis of (+)-giganin and its unnatural diastereoisomer (+)-C10-epi-giganin has been completed in a total of 13 linear steps, and 7 % and 8 % overall yield, respectively (see scheme; (-)-sp= (-)-sparteine, (+)-sps=(+)-sparteine surrogate). Lithiation–borylation methodology has been successfully applied in the key step, to couple together advanced intermediates with very high diastereoselectivity, thus demonstrating its power as a tool for total synthesis.

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