Pheromones of Coleoptera 13. Synthesis of racemic ferrulactone II from three easily accessible acetylenic precursors

Article abstract of DOI:10.1007/BF00698893

A ten-step synthesis of a racemic form of 3(Z),11(S)-dodecen-1-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 percent 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 as tert-butyl ethers has certain synthetic advantages. - Key words: (+/-)-3(Z)-dodecen-11-olide, synthesis; terminal alkynes, cross-coupling and C-alkylation; tert-butyl ethers, synthetic application.