Skeletal diversity via a folding pathway: synthesis of indole alkaloid-like skeletons.
Inspired by the skeletal diversity of naturally occurring indole alkaloids and the rich potential of chemistry developed by Padwa and co-workers, we conceived a pathway entailing six modes of intramolecular reactions leading to indole alkaloid-like skeletons. In this context, an efficient folding pathway via a rhodium-catalyzed tandem cyclization-cycloaddition involving three of the modes has been developed (two of which are shown above) that affords densely functionalized compounds with three distinct skeletons in a stereocontrolled manner.
Oguri
Hiroki
H
Howard Hughes Medical Institute, Department of Chemistry and Chemical Biology, Harvard University; Broad Institute of Harvard and MIT, Cambridge, Massachusetts 02138, USA.
Schreiber
Stuart L
SL
D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D026121:Indole Alkaloids