Stereochemical control of skeletal diversity.
[reaction: see text]. Substrates having appendages that pre-encode skeletal information (sigma-elements) can be converted into products having distinct skeletons using a common set of reaction conditions. The sequential use of the Ugi 4CC-IMDA reaction, followed by allylation, hydrolysis, and acylation of a chiral amino alcohol appendage (sigma-element), leads to substrates for a ROM/RCM or RCM reaction. The stereochemistry of the sigma-element and not its constitution controls the outcome of the pathway selected. This work illustrates the potential of linking stereochemical control to the challenging problem of skeletal diversity.
Sello
Jason K
JK
Department of Chemistry and Chemical Biology, Howard Hughes Medical Institute, Harvard Institute of Chemistry & Cell Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
Andreana
Peter R
PR
Lee
Daesung
D
Schreiber
Stuart L
SL
D002384:Catalysis; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D008968:Molecular Conformation; D015394:Molecular Structure; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism
D006576:Heterocyclic Compounds, 4 or More Rings; D012428:Ruthenium