American Chemical Society
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Hydrocarbon Oxidation vs C−C Bond-Forming Approaches for Efficient Syntheses of Oxygenated Molecules

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journal contribution
posted on 2005-01-20, 00:00 authored by Kenneth J. Fraunhoffer, Daniel A. Bachovchin, M. Christina White
A hydrocarbon oxidation approach has been applied to the construction of several linear (E)-allylic alcohols that have served as intermediates in the synthesis of natural products and natural product-like molecules. In the original syntheses, these intermediates were constructed using a standard Wittig-type olefination approach. We report here that routes to these same intermediates designed around a hydrocarbon oxidation approach are more efficient both in the total number of functional group manipulations (FGMs) and overall steps, as well as in the overall yield.