Premium
Gallium(III)‐Catalyzed Cycloisomerization Approach to the Diterpenoid Alkaloids: Construction of the Core Structure for the Hetidines and Hetisines
Author(s) -
Hamlin Amy M.,
de Jesus Cortez Felipe,
Lapointe David,
Sarpong Richmond
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.201209030
Subject(s) - cycloisomerization , stereocenter , stereochemistry , terpenoid , chemistry , indene , aldol reaction , core (optical fiber) , gallium , catalysis , organic chemistry , enantioselective synthesis , materials science , composite material
A versatile core structure has been prepared that should provide a foundation for the syntheses of the hetidine‐ and hetisine‐type diterpenoid alkaloids. The synthesis of the caged polycyclic core structure, which features nine contiguous stereocenters, utilizes a Ga III ‐catalyzed cycloisomerization of an alkynyl indene as well as a Michael/aldol sequence to build the bicyclo[2.2.2] framework.