A range of indole nucleophiles linked to amide and lactam functionality will be investigated for performance in the iridium catalyzed reductive cyclization cascades, and, based on successful proof of concept studies already performed in the Dixon group, a range of semi-saturated nitrogen-containing polycyclic structures possessing one or more stereocentres
distributed over an architecturally complex framework should result.
It contains 16 stereocentres
in the molecule, or carbon atoms to which different chemical groups or hydrogens can be attached in mirror image arrangements.
Their synthesis, which appeared in the Journal of the American Chemical Society (2003, 125, 9308), employs a tandem Diels-Alder/allylboration strategy which installs both stereocentres
and the heterocyclic ring rapidly and with high levels of enantiomeric control.
This has stimulated a chemical derivatization methodology to determine the configuration of the ten stereocentres
present in the molecule [7,8].