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A general synthesis of long chain ω- and (ω-1)-hydroxy fatty acids

✍ Scribed by Suzanne R. Abrams

Publisher
Elsevier Science
Year
1981
Tongue
English
Weight
294 KB
Volume
28
Category
Article
ISSN
0009-3084

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✦ Synopsis

A method for the synthesis of long chain fatty acids substituted at the to and to-1 positions has been developed. The key step is the isomerization of the triple bond of an alkyn-l-ol from an internal position in the chain to the free terminus with a new, convenient reagent, sodium aminopropylamide (NaAPA). Standard functional group manipulations i.e., Jones oxidation, esterification and hydroboration of the triple bond are used to prepare to-hydroxy fatty esters. The generality of the method is illustrated with syntheses of to-hydroxy fatty esters with 24, 26, 28 and 30 carbon chains.

In the 24 carbon series, hydration of the terminal triple bond of alkynoic ester 4a followed by reduction gave the (to-1)-hydroxy ester.

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