By John ApSimon
This, the 9th quantity of the "Total Synthesis of average items" sequence, involves a unmarried bankruptcy via ok. Mori analyzing the whole synthesis of insect pheromones.
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The whole Synthesis of common items Edited via John ApSimon quantity Six The 6th quantity during this renowned sequence considers the full synthesis of triterpenes, carbohydrates, fragrant steroids, pyrrole pigments and genes first stated through the interval from 1972 via 1982 during this sequence. 1984 (0 471-09900-7) 291 pp.
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Bestmann et al. 149Ranganathan et al. synthesized 36 starting from Indian castor oil (Scheme 95). I6l Methyl ricinoleate A, prepared from 38 (E:Z-06:4) Scheme 94 Indian castor oil NaoMe M~OH C0,Me > (48% ) ( 85% ) 6H ( 84% ) ( 80% ) H,C=CH(CH,),CO,Me A 8 36 ( E : 2 - 9 8 . 3 : 1 . 7 ) Scheme 95 TSOH ( 66% ) 7. 6% overall yield from castor Snider and Phillips used an ethylaluminum dichloride-catalyzed ene reaction of formaldehyde with 10-undecenyl acetate for the synthesis of 36 (Scheme 96). 163 ( 72% ) (E:2=78:22) 36 ( 65% ) Scheme 96 Several syntheses of 36 were based on sulfur chemistry as follows.
CH ,, \Cl 43 ( 96% ) (33%) Scheme 75 Rossi et al. employed the palladium-catalyzed coupling reaction of 1-alkenylborane with 1-bromoalkyne in their synthesis of 33 (Scheme 76). ) Scheme 76 A similar palladium-catalyzed coupling reaction of 1-alkenylborane with (2)1-iodo-I-butene was used by Cassani et al. ’44 > HCfC(CH,),OSiMe, THF 44 The Synthesis of Insect Pheromones, 1979-1989 Descoins et al. reported two syntheses of 33 employing organotransition metal chemistry. 145 In their first synthesis, coupling of (Z)-1-iodo- 1-butene and propargyl alcohol was followed by reduction to selectively give A (Scheme 78).
This was synthesized by the palladium-catalyzed Grignard-coupling reaction according to Linstrumelle (cf. 72A synthesis via acetylenic route was also reported. I l 4 K. (Z)-11-Hexadecenyl Acetate 29 (C18H3402) This is the pheromone of the purple stem borer (Sesamiu inferens), the diamond back moth (Plutella xylostella), and the cabbage moth (Momestra brussicae). 126A synthesis of 29 was reported by Tolstikov et al. 9eq 0, 2) H, I Lindlar-P ( 60% ) H H H .. \ I H .. c=c Me(CH,); LI,CUCI, (~ 5 % 29 \(CH2),,0A~ 30 Scheme 62 L.