Hydrocarbon oxidation vs C-C bond-forming approaches for efficient syntheses of oxygenated molecules.
[Reaction: see text] 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.
Fraunhoffer
Kenneth J
KJ
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Bachovchin
Daniel A
DA
White
M Christina
MC
D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D006838:Hydrocarbons / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry*
D000438:Alcohols; D006838:Hydrocarbons; D002244:Carbon; D010100:Oxygen