ISSN:
1573-9171
Keywords:
(±)-3(Z)-dodecen-11-olide, synthesis
;
terminal alkynes, cross-coupling andC-alkylation
;
tert-butyl ethers, synthetic application
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract A ten-step synthesis of a racemic form of 3(Z),1l (S)-dodecen-11-olide (ferrulactone II) has been developed. The synthesis is based on the Cadiot-Chodkiewicz cross-coupling of 4-pentyn-2-ol with 2-propyn-1-ol followed by carbon chain elongation by 3-butyn-1-ol and gives the target lactone in 9.7 % overall yield (based on the starting pentynol). All of the three building blocks used for the chain assembly are easily accessible from acetylene. The protection of OH groups astert-butyl ethers has certain synthetic advantages.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00698893
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