Stereoselective Total Synthesis of (+)‐Giganin and Its C10 Epimer by Using Late‐Stage Lithiation–Borylation Methodology | Zendy

Fletcher Catherine J. | Zendy; Wheelhouse Katherine M. P. | Zendy; Aggarwal Varinder K. | Zendy

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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.

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