SYNTHESIS OF THE PHEROMONES, (E)-3,7-DIMETHYL-2,7-OCTADIENYL PROPIONATE, (E)-3,7-DIMETHYL-2-OCTENE-1,8-DIOL AND FRONTALIN FROM A COMMON INTERMEDIATE
Ketal ester 9 has been prepared in five steps from methyl levulinate 4 (scheme 1).The propionate 1, diol 2 and (+/-) frontalin 3 were prepared from ester 9 employing the routes shown in scheme 2,3 and 4 respectively.The branched chain alkenes 13 and 20 were prepared conveniently from the primary alcohols 11 and 10 following the procedure of S.Wolff.Triethyl phosphonopropionate 7 has been prepared by methylating triethylphosphonoacetate with methyl iodide in the presence of sodium hydride.
Dhokte, U. P.,Rao, A. S.
p. 811 - 822
(2007/10/02)
REACTION OF HIGHLY ACTIVE MAGNESIUM WITH ISOPRENE, MYRCENE, OCIMENE, AND PIPERYLENE
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Cheskis, B. A.,Moiseenkov, A. M.,Struchkova, M. I.,Semenovskii, A. V.
p. 285 - 290
(2007/10/02)
SYNTHESIS OF ALLYLIC ALCOHOLS via ISOPRENE-, MYRCENE-, OCIMENE-, AND PIPERYLENE-MAGNESIUM COMPLEXES
Use of Rieke's active magnesium permits to achieve two-step conversion of the title dienes into respective allylic alcohols 1-11.
Moiseenkov, Alexander M.,Czeskis, Boris A.,Semenovsky, Alexei V.