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.
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.
Jason K
JK
Sello
Peter R
PR
Andreana
Daesung
D
Lee
Stuart L
SL
Schreiber
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