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Stereochemical control of skeletal diversity.


ABSTRACT: [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.

SUBMITTER: Sello JK 

PROVIDER: S-EPMC4134662 | BioStudies | 2003-01-01T00:00:00Z

REPOSITORIES: biostudies

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