54156-71-7Relevant academic research and scientific papers
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, 76. Synthesis of the Enantiomers of 10-Methyldodecyl Acetate and 12-Methyltetradecyl Acetate, Chiral Pheromone Components of Adoxophyes Species (Lepidoptera: Tortricidae)
Bestmann, Hans Juergen,Frighetto, Rosa T. S.,Frighetto, Nelson,Vostrowsky, Otto
, p. 829 - 831 (2007/10/02)
From enantiomeric (R)-(-)- and (S)-(+)-2-methylbutyl bromide (3), available by resolution of (R)-(-)-phenylglycinol amides of rac-2-methylbutanoic acid, and from enantiomeric 6-methyloctyl bromide (7) the corresponding phosphonium salts were obtained.Wittig olefination yielded the optically active methyl-branched olefinic THP ethers 12 and 13, hydrolysis, catalytic hydrogenation, and acetylation gave rise to the formation of the chiral title compounds (R)-(-)- and (S)-(+)-10-methyldodecyl acetate (1) and (R)-(-)- and (S)-(+)-12-methyltetradecyl acetate (2).
