TY - JOUR
T1 - Total Synthesis of (+)-Eburnamonine Using Asymmetric Alkene Cyanoamidation through C-CN Bond Activation
AU - DiLiberti, Serena L.
AU - Eastwood, Matthew S.
AU - Otte, Sadie C.
AU - Douglas, Christopher J.
N1 - Publisher Copyright:
© 2024 American Chemical Society
PY - 2024/7/12
Y1 - 2024/7/12
N2 - We report the total synthesis of (+)-eburnamonine using enantioselective alkene cyanoamidation to form the all-carbon quaternary stereocenter. Palladium, phosphoramidite ligand, and a Lewis acid combine to form a co-catalyst that promotes C-CN activation of a cyanoformamide, followed by intramolecular alkene cyanoamidation. Overall, the synthesis of (+)-eburnamonine is accomplished in 8 steps from 4-methylene hexanoic acid and tryptamine, providing an example of asymmetric aliphatic-tethered alkene cyanoamidation and its use in total synthesis.
AB - We report the total synthesis of (+)-eburnamonine using enantioselective alkene cyanoamidation to form the all-carbon quaternary stereocenter. Palladium, phosphoramidite ligand, and a Lewis acid combine to form a co-catalyst that promotes C-CN activation of a cyanoformamide, followed by intramolecular alkene cyanoamidation. Overall, the synthesis of (+)-eburnamonine is accomplished in 8 steps from 4-methylene hexanoic acid and tryptamine, providing an example of asymmetric aliphatic-tethered alkene cyanoamidation and its use in total synthesis.
UR - https://www.scopus.com/pages/publications/85197382246
UR - https://www.scopus.com/pages/publications/85197382246#tab=citedBy
U2 - 10.1021/acs.orglett.4c01480
DO - 10.1021/acs.orglett.4c01480
M3 - Article
C2 - 38950329
AN - SCOPUS:85197382246
SN - 1523-7060
VL - 26
SP - 5630
EP - 5634
JO - Organic Letters
JF - Organic Letters
IS - 27
ER -