INSECT PHEROMONES AND THEIR ANALOGUES. X. THE STEREODIRECTED SYNTHESIS OF (E,E)-DODECA-8,10-DIENOL

Article abstract of DOI:10.1007/BF00574341

A passage from deca-1,4,9-triene (I) to (E,E)-dodeca-8,10-dienol (II) in five stages with an overall yield of 23percent has been found by the selective transformations of deca-1,4,9-trien-1-yltrimethylsilane.Thus, under mild conditions, by the hydrogenation of (I) with the aid of 9-borabicyclo<3.3.1>nonane (9-BBN) followed by oxidation with H2O2 (E,E)-deca-6,8-dienol was obtained with a yield of 60percent, and this was converted quantitatively into the corresponding tosylate.The ethynylation of the latter with lithium acetylide gave (E,E)-dodecadien-1-yne (III) on a Lindlar catalyst followed by the reaction of the resulting triene with 9-BBN, as described above for (I) led to the desired codlemone (II).The IR, PMR, 13C NMR, UV, and mass spectra of the compound obtained are discussed.