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Gram‐Scale Synthesis of the (−)‐Sparteine Surrogate and (−)‐Sparteine
Author(s) -
Firth James D.,
Canipa Steven J.,
Ferris Leigh,
O'Brien Peter
Publication year - 2018
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.201710261
Subject(s) - sparteine , yield (engineering) , chemistry , combinatorial chemistry , gram , organic chemistry , materials science , biology , bacteria , metallurgy , genetics
An 8‐step, gram‐scale synthesis of the (−)‐sparteine surrogate (22 % yield, with just 3 chromatographic purifications) and a 10‐step, gram‐scale synthesis of (−)‐sparteine (31 % yield) are reported. Both syntheses proceed with complete diastereocontrol and allow access to either antipode. Since the syntheses do not rely on natural product extraction, our work addresses long‐term supply issues relating to these widely used chiral ligands.