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Stereoselective Total Synthesis of (+)‐Giganin and Its C10 Epimer by Using Late‐Stage Lithiation–Borylation Methodology
Author(s) -
Fletcher Catherine J.,
Wheelhouse Katherine M. P.,
Aggarwal Varinder K.
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201208403
Subject(s) - borylation , total synthesis , chemistry , stereoselectivity , epimer , diastereomer , yield (engineering) , stereochemistry , sparteine , medicinal chemistry , organic chemistry , aryl , catalysis , thermodynamics , alkyl , physics
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.