Stereochemical control of skeletal diversity.

Org Lett
Authors
Keywords
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.

Year of Publication
2003
Journal
Org Lett
Volume
5
Issue
22
Pages
4125-7
Date Published
2003 Oct 30
ISSN
1523-7060
DOI
10.1021/ol035773h
PubMed ID
14572265
PubMed Central ID
PMC4134662
Links
Grant list
F32 GM070253 / GM / NIGMS NIH HHS / United States