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By John ApSimon

This, the 9th quantity of the "Total Synthesis of average items" sequence, contains a unmarried bankruptcy via ok. Mori analyzing the full synthesis of insect pheromones.

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By John ApSimon

This, the 9th quantity of the "Total Synthesis of average items" sequence, contains a unmarried bankruptcy via ok. Mori analyzing the full synthesis of insect pheromones.

Show description

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Extra resources for The Total Synthesis of Natural Products (Volume 9)

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PHEROMONE HYDROCARBONS AND ACETATES WITH A 2-DOUBLE BOND A. Muscalure, (23-9-Tricosene 19 ((&H4,) This is the female-produced sex pheromone of the house fly (Musca domestica). Many new syntheses of 19 have been published based on carbanion chemistry, organotransition metal chemistry, organoborane chemistry, etc. Naoshima et al. 9' Scheme 36 26 The Synthesis of Insect Pheromones, 1979-1989 Yadav et al. ,-K’...... 5) 1) FB(OMe), 6.. Me(CH,),CH-CH-CH, I-BuOK 2) 40, 3)Ac,O H \ /C Cul Me(CH,), Scheme 38 /H c, = C\ = c, I 19 H (CH2)44e The first Scheme 38 illustrates the synthesis of 19 by Schlosser’s approach is the use of “instant ylide,” which is a mixture of sodium amide and the phosphonium salt.

32,5E)-3,5-TetradecadienylAcetate 38 (C16H2802) This is the sex pheromone of the carpenter worm moth (Prinoxystus robiniae). Rossi et al. synthesized 38 by a palladium-catalyzed reaction (Scheme 107). Pd(PPh3), , Cul H, C = CI I k M~(cH,),' f H, 10% NaOH , CH ,, HCEC(CH,),OH PhCH,NE\CI c=c' Me(CH,); ( 85% 1 H ' ( 73% ) ( 97% ) C Z C(CH,),OH 38 Scheme 107 By employing their stereoselective formylolefination method with triphenylarsonium ylide, Huang et al. 137Preparation of Me(CH,),CHO + [Ph+'CH,CHO]Bi &CO,/ baca H 2 0 1) [Ph3P'(CH2),0THP]Bi n-BuU / THF HMPA .

E)-g-Dodecenyl Acetate 14 (C,4H2602) This is the pheromone component of the red bollworm moth (Diparopsis castanea) and the cereal tortrix moth (Cnephasia purnicana). The European pine shoot moth (Rhyacionia buoliana) also uses 14 as its pheromone. Bestmann et al. 84 H MeC=CCH,Br H (W3P > OP(OEt), H I MeC=CCH(CH,),OTHP H H EtC=C(CH,),OH H 0 H II MeC=CCH,P(OEt), H LIAIH, > - EbO 2) Br(CH,),OTHP H EtC=C(CH,),OTHP H , Ac,O/C,H,N 1) n-BuLi ____a TsOH aq MeOH (33% overall) Et\ (72%) >- H / c=c \ HI (CH,),OAc 14 Scheme 31 E.

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