53645-21-9Relevant academic research and scientific papers
BOTPPI, a new Wittig salt for the synthesis of 12-(S)-hydroxy- eicosatetraenoic acid [12-(S)-HETE]
Christiansen, Michael A.,Andrus, Merritt B.
supporting information; experimental part, p. 4805 - 4808 (2012/09/22)
An efficient route to (Z)-(8-benzyloxy-8-oxooct-3-en-1-yl) triphenylphosphonium iodide, or BOTPPI, is disclosed, complete with full experimental details, NMR spectra, and HRMS data. BOTPPI serves as a surrogate for (Z)-(8-methoxy-8-oxooct-3-en-1-yl)triphe
5-F2t-isoprostane, a human hormone?
Taber, Douglass F.,Kanai, Kazuo,Pina, Richard
, p. 7773 - 7777 (2007/10/03)
Syntheses of the four enantiomerically pure diastereomers of 5-F2t-isoprostane (5-8) are described. The key step is the lipase-catalyzed chemo-enzymatic resolution of the racemic diol 40 to give the mono-acetates 41 and 42. The enantiomerically
EXO- AND ENDOHORMONES, XVI SYNTHESIS OF (4E, 7Z)-4,7-TRIDECADIEN 1-YL ACETATE, THE SEX PHEROMONE FOR THE LEAFMINER LITHOCOLLETIS CORYLIFOLIELLA
Gocan, Alexandra,Gansca, Lucia,Oprean, Ioan
, p. 253 - 258 (2007/10/03)
The synthesis of the sex pheromone of the leafminer moth, Lithocolletis corylifoliella, (4E, 7Z)-4,7-tridecadien-1-yl acetate, was based on a C5+C8 scheme.The coupling reaction took place between the Grignard reagent of 4-pentin-1-1-oic acid and 1-bromo-2Z-octene.Propargylic alcohol was used as a starting material in order to obtain the two synthons.
DIRECT CONVERSION OF TETRAHYDROPYRANYLATED ALCOHOLS TO THE CORRESPONDING BROMIDES
Wagner, A.,Heitz, M.-P.,Mioskowski, C.
, p. 557 - 558 (2007/10/02)
Various tetrahydro-2 pyranyl protected alcohols are converted into the corresponding bromides by PPh3/CBr4, with inversion of configuration, and high in yield.
PREPARATIVE SYNTHESIS OF TOSYLATES OF UNSATURATED ALCOHOLS AND UNSATURATED BROMIDES UNDER PHASE TRANSFER CONDITIONS
Ishchenko, R. I..,Kovalev, B. G.,Khusid, A. Kh.
, p. 1076 - 1078 (2007/10/02)
A preparative synthetic method has been developed for tosylates of unsaturated alcohols and their conversion to bromides under phase transfer conditions in the case of alkyn-1-ols, E- and Z-alken-1-ols, 3-methyl-3-buten-1-ol and cyclopropylmethanol.
The Preparation of Some Octenyl Sulfides from Oct-1-en-3-ol and Oct-2-en-1-ol
Binns, Malcolm R.,Haynes, Richard K.,Lambert, Dale E.,Schober, Paul A.,Turner, Susan G.
, p. 281 - 290 (2007/10/02)
(E)- and (Z)-1-(Phenylthio)oct-2-ene, (E)-1-(methylthio)- and 1-(t-butylthio)-oct-2-ene, S- N,N-dimethylthiocarbamate, S- N,N-dimethylthiocarbamate, (E)-(oct-2-enylthio)benzothiazole, and S- N,N,N',N'-tetramethylphosphorodiamidothioate have been prepared by nucleophilic substitution reactions and - and -sigmatropic shifts involving intermediates prepared from oct-1-en-3-ol and (E)- and (Z)-oct-2-en-1-ol.
ALLYLATION OF GRIGNARD REAGENTS: ITS APPLICATION FOR THE SYNTHESIS OF (4E,7Z)-4,7-TRIDECADIENYL ACETATE, A SEX PHEROMONE OF POTATO TUBERWORM MOTH
Yadav, J. S.,Reddy, P. Satyanarayana
, p. 1119 - 1132 (2007/10/02)
Alkylmagnesium halides have been found to react with (Z)-4-benzyloxy-1-chloro-2-butene in presence of HMPA to produce a rearranged product 3-alkyl-4-benzyloxy-1-butene, while the absence of HMPA a normal product (Z)-1-alkyl-4-benzyloxy-2-butene resulted as the predominant product.Latter product has been utilized for the synthesis of (4E,7Z)-4,7-tridecadienyl acetate, a sex pheromone of potato tuberworm moth.
Total Synthesis of (+/-)-12-Hydroxy-5(Z),8(Z),10(E),14(Z)-eicosatetraenoic Acid (12-HETE)
Gunn, Bruce P.,Brooks, Dee W.
, p. 4417 - 4418 (2007/10/02)
A total synthesis of 12-HETE is reported which incorporates an oxidative cleavage of an appropriately substituted furan to provide a functionalized trans-allylhydroxy fragment which is subsequently elaborated in an operationally simple manner affording a practical preparation of 12-HETE.
Synthesis of Heptadeca-1,8Z,11Z-triene
Vig, O. P.,Sharma, M. L.,Kumari, Sarla,Rani, Veena
, p. 769 - 770 (2007/10/02)
The bromide (III), obtained from oct-2Z-en-1-ol (II) by treatment with PBr3/pyridine, reacts smoothly with 3-(tetrahydro-2-pyranyloxy)propynylmagnesium bromide to give IV which loses the protective pyranyl moiety when reacted with PTS/methanol to yield the alcohol (V).Catalytic hydrogenation of V in the presence of Lindlar's catalyst affords the dienol (VI) which is converted into the corresponding mesylate (VII) on reaction with MsCl/TEA.Coupling of VII with hex-1-enylmagnesium bromide in THF/HMPA at 0 deg C provides the title compound (I).
A Convenient Synthesis of (Z)-5-Undecen-2-one, Sex Pheromone from the Pedal Gland of Bontebok
Trehan, I. R.,Kad, G. L.,Varma, Neena,Singh, Labh
, p. 1273 - 1274 (2007/10/02)
Oct-2-yn-1-ol (II) on catalytic hydrogenation over 5percent Lindlar's catalyst yields (Z)-2-octen-1-ol (III) which is transformed into 1-bromo-2(Z)-octene (IV) by treatment with PBr3.Alkylation of α-lithioacetone dimethylhydrazone with IV in THF at -78 deg C followed by hydrolysis of the resulting hydrazone with NaIO4 at pH 7 results in formation of the title compound (I).
