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The Journal of Organic Chemistry Jun 2021-Dihydroxylation of trinor-18α-olean-17(22)-ene with osmium tetroxide led to diol . Its cleavage with lead tetraacetate gave tetracyclic ketoaldehyde . By comparison,...
-Dihydroxylation of trinor-18α-olean-17(22)-ene with osmium tetroxide led to diol . Its cleavage with lead tetraacetate gave tetracyclic ketoaldehyde . By comparison, the ozonation of trinor-18α-olean-17(22)-ene in the presence of -toluenesulfonic acid gave the corresponding ketoacetal . Both products were subjected to an intramolecular aldol reaction under the acidic conditions and yielded unusual triterpenes bearing a bicyclo[4.3.1]decane fragment (). Further manipulation of the protective groups afforded compounds useful in triterpene synthesis, especially in the preparation of potentially biologically active saponins based on a tetracyclic terpene core.
Topics: Aldehydes; Oxidative Stress; Saponins; Triterpenes
PubMed: 34033473
DOI: 10.1021/acs.joc.1c00697