129594-53-2Relevant academic research and scientific papers
Highly Stereocontrolled Total Synthesis of Leukotriene B4, 20-Hydroxyleukotriene B4, Leukotriene B3, and Their Analogues
Kobayashi, Yuichi,Shimazaki, Toshiyuki,Taguchi, Hideki,Sato, Fumie
, p. 5324 - 5335 (1990)
A highly stereocontrolled and practical new method for synthesis of LTB4 (1), 20-OH-LTB4 (2), and LTB3 (3) has been developed, which uses the palladium catalyzed coupling reaction of the vinylborane 5, derived from the C(1)-C(9) fragment 4, with the corresponding C(10)-C(20) fragments 6a-c.The acetylene 4 was synthesized by palladium-copper-catalyzed coupling reaction of (trimethylsilyl)acetylene with the bromide 12, which was prepared from γ-(trimethylsilyl)allylic alcohol (S)-10 by bromination followed by debromosilylation.The alcohol (S)-10 was obtained by the kinetic resolution of the racemate dl-10 using the Sharpless reagent.The vinyl iodides 6a and 6b were prepared from racemic γ-(trimethylsilyl)allylic alcohols dl-17 and dl-28, respectively, by the Sharpless kinetic resolution followed by the reactions taking advantage of the reactivity of vinylsilane moiety, while the segment 6c was prepared by the Sharpless kinetic resolution of racemic γ-iodoallylic alcohol dl-34 followed by protection.By using this method, precursors of the radiolabeled LTB4, and 20-OH-LTB4, i.e., 14,15-didehydro-LTB4 (40) and 14,15-didehydro-20-OH-LTB4 (41), respectively, were also synthesized.Similarly the novel structural analogue of LTB 42-44 were prepared.
3-Substituted iodo alkenyl compounds and methods for preparing same
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, (2008/06/13)
Compounds of the formula: SPC1 Where R is hydrogen, methyl or ethyl; R' is hydrogen, a saturated hydrocarbon chain containing from 1 to about 9 carbon atoms, pentene, hexene, cyclohexyl, or benzyl X is hydrogen, pyranoxy, OR" where R" is a hydrocarbon chain containing from 1 to about 5 carbon atoms or benzyl, EQU1 where R"' is a hydrocarbon chain containing from 1 to about 8 carbon atoms or benzyl, or EQU2 where R1 and R2 are each a hydrocarbon chain containing from 1 to about 5 carbon atoms, and n is an integer from 0 to 5 These compounds are key intermediates in the production of prostaglandins and exhibit antibacterial properties.
