Abstract
Highly enantiomerically enriched ( R)-incrustoporin was enantioselectively synthesized in 43.6% overall yield starting from 4-iodotoluene. The key steps of the synthesis included the asymmetric hydrogenation of 1-( p-tolyl)-1-pentyn-3-one catalyzed by a non-racemic Ru(II) complex and the Pd-catalyzed cyclocarbonylation of so-obtained highly enantiomerically enriched 1-( p-tolyl)-1-pentyn-3-ol. This Pd-catalyzed reaction, whose stereochemical outcome was previously unknown, proceeded with retention of configuration and 2.5% or less racemization. The enantiomeric purities of ( R)-1-( p-tolyl)-1-pentyn-3-ol and ( R)-incrustoporin were evaluated by HPLC analysis on a Chiralcel OJ column as well as by performing the 1H NMR spectra of these compounds in a D 2O solution which was saturated with α- or β-cyclodextrin, respectively.
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