95451-56-2Relevant academic research and scientific papers
INSECT PHEROMONES AND THEIR ANALOGUES. X. THE STEREODIRECTED SYNTHESIS OF (E,E)-DODECA-8,10-DIENOL
Odinokov, V. N.,Balezina, G. G.,Ishmuratov, G. Yu.,Salimgareeva, I. M.,Bogatova, N. G.,et al.
, p. 486 - 489 (1984)
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-borabicyclononane (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.
