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Transformation from intermediate 3 to 4 in the synthesis of Vinigrol

Maimone, T. J.; Shi, J.; Ashida, S.; Baran, P. S. J. Am.Chem. Soc. 2009, 131, 17066-17067.

 

We decided that peak a would be on the sp2 double bond Hydrogen because that is the approximate range expected for sp2 Hydrogens. Hb was on an alcohol group, which means it would be downfield shifted as well. Hc is the bonded to the most highly substituted carbon, so it would be the next most downfield shifted peak. The rest of the Hydrogens were placed based on carbon substitution and proximity to double bonds/alcohol groups.

The assignment for the alcohol and adjacent Hydrogen could not be determined because there were no peaks in the expected range on the 1H-NMR. Also, the Hydrogens given in the Experimental procedure totaled up to 26, but there were 28 expected Hydrogens on compound 4.