58257-21-9Relevant articles and documents
Total synthesis of infectopyrone, aplysiopsenes A-C, ent-aplysiopsene D, phomapyrones A and D, 8,9-dehydroxylarone, and nectriapyrone
Geiseler, Oliver,Podlech, Joachim
experimental part, p. 7280 - 7287 (2012/09/11)
The total synthesis of the 2-pyrone natural products nectriapyrone, aplysiopsenes A-C, ent-aplysiopsene D, phomapyrones A and D, and of 8,9-dehydroxylarone were achieved by Wittig olefination starting with vermopyrone. Infectopyrone was synthesized by Horner-Wadsworth-Emmons reaction starting with phomapyrone D. Racemic phomapyrone C methyl ether was obtained by hydrogenation of nectriapyrone. The total syntheses were achieved starting from commercially available 3,5-heptanedione and led to the desired natural products in 18-46% over 5-6 steps, whereupon all five-step syntheses were carried out with a single chromatographic workup. The total synthesis of infectopyrone, aplysiopsenes A-D, of phomapyrones A and D, and of 8,9-dehydroxylarone were achieved for the first time, giving unambiguous proof for the proposed structures of these natural products.
Pheromones, 89.- Wittig Syntheses of Alkyl-Branched and Cyclic Analogs of (Z)-5-Decenyl Acetate, the Sex Pheromone of Agrotis segetum (Lepitoptera: Noctuidae)
Albores, Martha,Bestmann, Hans Juergen,Doehla, Bodo,Hirsch, Hans-Ludwig,Roesel, Peter,Vostrowsky, Otto
, p. 231 - 236 (2007/10/02)
By means of (Z)-selective Wittig olefination alkyl-branched and cyclic analogs of (Z)-5-decenyl acetate, the sex pheromone of the turnip moth, Agrotis segetum (Lepidoptera: Noctuidae), have been synthesized. Key Words: Pheromones / (Z)-5-decenyl acetate / Wittig reactions / Agrotis segetum
EFFECTIVE SYNTHESIS OF (4R,8R)- AND (4R,8S)-ENANTIOMERS OF 4,8-DIMETHYLDECANAL, THE AGGREGATIONAL PHEROMONE OF THE BEETLES TRIBOLIUM CONFUSUM AND TRIBOLIUM CASTANEUM
Cheskis, B. A.,Lebedeva, K. V.,Moiseenkov, A. M.
, p. 745 - 751 (2007/10/02)
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