TY - JOUR
T1 - Iterative Synthetic Strategy for Azaphenalene Alkaloids. Total Synthesis of (-)-9a epi-Hippocasine
AU - Alujas-Burgos, Sílvia
AU - Oliveras-González, Cristina
AU - Álvarez-Larena, Ángel
AU - Bayón, Pau
AU - Figueredo, Marta
PY - 2018/5/4
Y1 - 2018/5/4
N2 - © 2018 American Chemical Society. A new strategy for the stereoselective synthesis of alkaloids with perhydro-9b-azaphenalene skeleton has been developed. The starting material is the substituted glutarimide derivative 1, readily available in either enantiomeric form through the palladium-catalyzed asymmetric allylic alkylation of glutarimide. The strategy relies on an iterative methodology encompassing two nucleophilic allylations and two ring closing metathesis processes. The approach has been used in the first synthesis of (-)-9a-epi-hippocasine.
AB - © 2018 American Chemical Society. A new strategy for the stereoselective synthesis of alkaloids with perhydro-9b-azaphenalene skeleton has been developed. The starting material is the substituted glutarimide derivative 1, readily available in either enantiomeric form through the palladium-catalyzed asymmetric allylic alkylation of glutarimide. The strategy relies on an iterative methodology encompassing two nucleophilic allylations and two ring closing metathesis processes. The approach has been used in the first synthesis of (-)-9a-epi-hippocasine.
U2 - https://doi.org/10.1021/acs.joc.8b00390
DO - https://doi.org/10.1021/acs.joc.8b00390
M3 - Article
VL - 83
SP - 5052
EP - 5057
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 9
ER -