- INSECT PHEROMONES AND THEIR ANALOGUES. XXII. METHYL-BRANCHED PHEROMONES BASED ON 4-METHYLTETRAHYDROPYRAN. SYNTHESIS OF RACEMIC 2-ACETOXY-3,7-DIMETHYLPENTADECANE (DIPRIONYL ACETATE)
-
A synthesis is proposed of racemic 2-acetoxy-3,7-dimethylpentadecane - the sex attractant (diprionyl acetate) of plane sawflies of the genera Diprion and Neodiprion on the basis of the regioselective transformation of bifunctional products of the cleavage of 4-methyltetrahydropyran.
- Odinokov, V. N.,Ishmuratov, G. Yu.,Kharisov, R. Ya.,Tolstikov, G. A.
-
-
Read Online
- INSECT PHEROMONES AND THEIR ANALOGUES. XXXVIII. SYNTHESIS OF (+/-)-3-METHYLHENEICOSAN-2-ONE AND (+/-)-2-ACETOXY-3,7-DIMETHYLPENTADECANE USING THE REDUCTIVE β-VINYLATION OF α-OLEFINS
-
Schemes are proposed for the synthesis of (+/-)-3-methylheneicosan-2-one and (+/-)-2-acetoxy-3,7-dimethylpentadecane - racemic analogues of the sex pheromones of the common cockroach (Blatella germanica) and of plane sawflies of the genera Diprion and Neodiprion, respectively, using the reductive β-vinylation of α-olefins.
- Odinokov, V. N.,Ishmuratov, G. Yu,Ibragimov, A. G.,Yakovleva, M. P.,Zolotarev, A. P.,et al.
-
p. 496 - 499
(2007/10/02)
-
- INSECT PHEROMONES AND THEIR ANALOGUES XXIV. SYNTHESIS OF LONG-CHAIN 1,5-DIMETHYL-BRANCHED PHEROMONES FROM GERANYL ACETATE
-
Schemes for the synthesis of long-chain 1,5-dimethyl-branched pheromones (7,11-dimethyloctadecane, 15,19-dimethyltritriacontane, and 2-acetoxy-3,7-dimethylpentadecane) from the product of allyl oxidation of geranyl acetate (8-acetoxy-2,6-dimethylocta-2E,6E-dien-1-ol) have been developed.
- Odinokov, V. N.,Ishmuratov, G. Yu.,Ladenkova, I. M.,Tolstikov, G. A.
-
p. 697 - 701
(2007/10/02)
-
- OZONOLYSIS OF ALKENES AND REACTIONS OF POLYFUNCTIONAL COMPOUNDS. XXX. SYNTHESIS OF THE ACETATE OF DIASTEREOMERIC (+/-)-3,7-DIMETHYLPENTADECAN-2-OL AND ITS 7-NOR ANALOG - THE SEX PHEROMONES OF PINE SAWFLIES OF THE DIPRION AND NEODIPRION GENUS
-
6-Methyltetradecan-2-one was obtained on the basis of the selective transformations of 4-methyl-1,8-dioxo-4Z-nonene (the product from partial ozonolysis of 1,5-dimethyl-1Z,5Z-cyclooctadiene).Olefination of the product and of its 6-nor analog with ethylidenetriphenylphosphorane, followed by hydration of the double bond through hydroboranation, led to the synthesis of the diastereomeric (+/-)-3,7-dimethylpentadecan-2-ol and its 7-nor analog and their acetates, i.e., the sex pheromones of pine sawflies of the Diprion and Neodiprion genus.
- Odinokov, V. N.,Akhmetova, V. R.,Ishmuratov, G. Yu.,Botsman, L. P.,Tolstikov, G. A.
-
p. 851 - 855
(2007/10/02)
-