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The esterification of sterically hindered or non-nucleophilic alcohols may often be problematic. The reaction of alcohols with acid fluorides is reported to be superior to standard acid activation protocols frequently used for difficult esterifications. The acid fluoride methodology was used to produce a hindered linkage between a secondary alcohol (4) and a cyclohexyl amino acid 3, a key intermediate in the formation of a constrained ring didemnin analog.
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