1,11-Dodecadiene

If cyclooctene conversion achieved 93%, a mixture of 1,9-dodecadiene had 7JE stereocontent 50/50. We have used this mixture for preparation of accurate copies of natural pheromones of cherry bark tortix moth (Enarmonia formasana) according to the Scheme 3. 

The trisannulation reagent 7-acetoxy-l,l l-dodecadien-3-one (134) is derived from the bisannulation reagent 124 in four steps. This reagent is a synthetic equivalent of l-dodecene-3,7,11-trione, and the two ketone groups of the trione are masked as an acetoxy and a terminal alkene. The synthesis of optically active D-homo-19-norandrosta-4-en-3-one (135) by the trisannulation reaction... 

The preparation of the sex pheromone of the bollworm moth, ( )-9,ll-dodecadien-l-yl acetate, from compound A has been described. Suggest suitable reagents for each step in this sequence. 

However, this behavior cannot be depended on. It is safer to monitor hydrogen uptake. Reduction of 4-oxo-slowed down at the ethylene stage although in other compounds, the same catalyst did give spontaneously selective reductions. 

Farnesyl, 10-bromo-10,l 1-dihydro-l 1-hydroxy-, acetate [2,6-Dodecadiene-1,11-diol, 10-bromo-3,7,11-trimethyl-, 1-acetate, ( , )-], 113 Ferrocene, 28... 

Aus 2-Methyl-dodecadiin-(3,5) erhalt man mit zwei Mol-Aquivalenten Dicyclohexyl-boran und Protonolyse 2-Methyl-cis,cis-dodecadien-(3,5)2 (74% d.Th. Kp3 80°). (Wei-teres iiber die Reaktion s.ds. Handb., Bd. V/lb, S. 799ff.) ... 

Recent trend in the synthesis of olefinic pheromones is the use of transition metal-catalyzed cross coupling reaction for carbon-carbon bond formation. Scheme 8 summarizes a synthesis of the termite trail marker pheromone, (3Z,6Z)-3,6-dodecadien- l-ol (2) by Oehlschlager [19]. The key-step is the palladium-catalyzed cross-coupling of allylic chloride A and alkenylalane B. 

Comparative GC, GC-EAD and GC-MS analyses of extracted Setora nitens (nettle caterpillars) compounds and authentic standards showed that the candidate pheromone components were ( )-9-dodecenal and (-Z)-9,11 dodecadienal. The other two EAD-active compounds were the corresponding alcohols of these aldehydes. ... 

Finally, a Japanese group also studied the biotransformation of Z- and -nerolidol [137,138] with the plant pathogenic fungus Glomerella cingulata. Both Z- and -nerolidol were mainly oxidised at the remote double bond. Z-Nerolidol (162) was transformed into (Z)-3,7,11-trimethyl-l,6-dodecadiene-3,10,11-triol (164) while -nerolidoI (158) was mainly oxidised to ( )-3,7,11-trimethyl-l,6-dodecadiene-3,ll-diol (171) only small amounts of ( )-3,7,11-trimethyl-l,6-dodecadiene-3,10,11-triol (160) were obtained, Fig. (34). 

More recently, the biotransformation of (2 ,6 )-famesol (181a) was also carried out by a Japanese group [141] using the fungus Glomerella cingulata. At the first step, oxidation proceeded at the remote double bond to give (2.E,6 )-3,7,11 -trimethyl-2,6-dodecadien-l,l 1-diol (184) and (22 , 6E)-3,7,11 -trimethyl-2,6-dodecadien-l,10,ll-triol (185). In the second step, the diol (184) was further hydroxylated to (22 ,62s)-3,7,ll-trimethyl-2,6-dodecadien-l,5,ll-triol (186), which was further isomerised to its (2Z,6 )-isomer (187), Fig. (36). 

Butene 4-Cyclohexyl-2-ethoxy-1.1,1-trifluoro- ElOb, 459 (F3C-COOR + -CH2-R) 2,4-Dodecadiene 12-Hydroxy-l,l,l-trifluoro- E10b2, 176f. (2-In —> 2,4-Dien)... 

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