16695-34-4Relevant articles and documents
Synthesis of Trans Olefins by a Nickel-Catalyzed Reduction of Enol Ethers. A Formal, Total Synthesis of (+/-)-Recifeiolide
Ducoux, Jean-Philippe,Menez, Patrick Le,Kunesch, Nicole,Wenkert, Ernest
, p. 1290 - 1292 (1993)
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Insect pheromones and their analogs. LVIII. Synthesis of hexadeca-7Z,11E-dien-1-yl acetate - A component of the sex pheromones of Pectinophora gossypiella and Sitotroga cerealella
Odinokov,Vakhidov,Shakhmaev,Zorin
, p. 186 - 188 (1998)
A new synthesis of hexadeca-7Z,11E-dien-1-yl acetate - a component of the sex pheromones of the pink bollworm (Pectinophora gossypiella) and the Angoumois grain moth (Sitotroga cerealella) - is proposed that is based on a thermal Claisen rearrangement. Scientific-Research Institute of Small-Tonnage Chemical Products and Reagents, Ufa, fax 8-(3472) 43 17 31.
STEREOSELECTIVE AND VERSATILE APPROACH FOR THE SYNTHESIS OF GOSSYPLURE AND ITS COMPONENTS
Joshi, N. N.,Mamdapur, V. R.,Chadha, M. S.
, p. 3285 - 3290 (1984)
Efficient synthetic routes to gossyplure and its components (1a and 1b) were formulated.The three key units viz the alkynol 3, the bromide 5, and the alkanal 13 were derived from easily accessible starting materials.Alkylation of 3 with 5, and subsequent semihydrogenation followed by oxidation, provided the C11-alkenal 8 which was subjected to a stereocontrolled Wittig reaction with a C5-phosphonium salt, to yield directly the disired pheromone (1a + 1b).The synthesis of its individual components involved the manipulation via an acetylenic intermediate, viz the alkynol 14 which was obtained through alkylation of 3.A sequence of well-established reactions on 14, then provided the corresponding (E)- and (Z)-alkenylphosphonium salts which upon a (Z)-specific Wittig olefination with the C7-aldehyde (13), led to the stereoselective synthesis of 1a and 1b.
Access to Saturated Thiocyano-Containing Azaheterocycles via Selenide-Catalyzed Regio-A nd Stereoselective Thiocyanoaminocyclization of Alkenes
Wei, Wei,Liao, Lihao,Qin, Tian,Zhao, Xiaodan
, p. 7846 - 7850 (2019/10/10)
An efficient route for the synthesis of saturated thiocyano-containing azaheterocycles by selenide-catalyzed regio-A nd stereoselective thiocyanoaminocyclization of alkenes is disclosed. The desired products were obtained in moderate to high yields under mild conditions. The generality of this method was elucidated by its efficient application in thiocyano oxycyclization of alkenes.
A facile access to bridged 1,2,4-trioxanes
Zhang, Qi,Jin, Hong-Xia,Wu, Yikang
, p. 11627 - 11634 (2007/10/03)
Bicyclo[3.2.1] type 1,2,4-trioxanes are readily synthesized from precursors that may form intramolecular hemiketals using UHP (H2O2-urea complex) as the source of the peroxy bond and p-TsOH or CSA as the catalyst. The ring closure through an intramolecular Michael addition occurred in a highly stereoselective way, giving only one diasteromer as shown by the NMR spectra.
Synergistic sex pheromone components of white-spotted tussock moth, Orgyia thyellina
Gries, Gerhard,Clearwater, John,Gries, Regine,Khaskin, Grigori,King, Skip,Schaefer, Paul
, p. 1091 - 1104 (2007/10/03)
In 1996, the exotic white-spotted tussock moth (WSTM), Orgyia thyellina (Lepidoptera: Lymantriidae), was discovered in Auckland, New Zealand. Because establishment of WSTM would threaten New Zealand's orchard industry and international trade, eradication of WSTM with microbial insecticide was initiated. To monitor and complement eradication of WSTM by capture of male moths in pheromone-baited traps, pheromone components of female WSTM needed to be identified. Coupled gas chromatographic-electroantennographic detection analysis of pheromone gland extract revealed several compounds that elicited responses from male moth antennae. Mass spectra of the two most EAD-active compounds suggested, and comparative GC-MS of authentic standards confirmed, that they were (Z)-6-heneicosen-11-one (Z6-11-one) and (Z)-6-heneicosen-9- one, the latter termed here 'thyellinone.' In field experiments in Japan, Z6- 11-one plus thyellinone at a 100:5 ratio attracted WSTM males, whereas either ketone alone failed to attract a single male moth. Addition of further candidate pheromone components did not enhance attractiveness of the binary blend. Through the 1997-1998 summer, 45,000 commercial trap lures baited with 2000 μg of Z6-11-one and 100 μg of thyellinone were deployed in Auckland towards eradication of the residual WSTM population.
