(+)-2,3,5-Tdchloro-4,4-ethylenedioxycyelopent-2-en-l-one reacts with Me2CuCNLi 2 to give depending on conditions the corresponding 3-methyl substituted cyclopentenone (AdffE adduet) or a mixture of unsaturated acyelic acids formed as the result of abnormal cleavage reaction of C(1)--C(2) bond in the trichorocyclopentenone. Reactions of conjugated 1,4-addition of Me2CuCNLi 2 to (_+)-5-allyl-2,3,5-trichloto-4,4-dimethoxycyclopent-2-enl-one lead to products of replacement of vinylic CI atom at C(3) by Me group and those of C(5)-dechlorination.
Ermisoprostol (I),Below we report on the comparative investigation of the antiulcerous activity of compounds I and II. Misoprostol was synthesized according to the cuprate scheme using enone III and a high-order cuprate reagent IV. The corresponding precursors, hydroxyenone V and vinylstaunane VI, were synthesized as described in [4,5].The 1,4-conjugation of compound IV to enone HI proceeded quite rapidly (5-10rain) at-60...-30~ After acid deblocking of protective groups in the cuprate synthesis product under mild conditions, a triple chromatographic purification on silica gel gives compound I at a 40% yield. The HPLC analysis of this product showed a Cl6-diastereomer ratio of 6 : 4. According to [6], misoprostol obtained by the cu-
Reactions of SodiumDiethyl Malonate with Functionalized 2,3-Dichlorocyclopentenones. Preparation of Water-Soluble Derivatives. -The title reaction yields the expected products (III) and (V) of Ad N Esubstitution of vinylic chlorine at C-3. -(IVANOVA, N. A.; SHAINUROVA, A. M.; AKHMETVALEEV, R. R.; BELOGAEVA, T. A.; MIFTAKHOV, M. S.; Russ.
Reaction of Dimethylsulfoxonium Methylide with 5-Allyl-2,3,5trichloro-4,4-dimethoxycyclopent-2-en-1-one.-Dimethylsulfoxonium methylide, generated in situ from sulfoxonium iodide (II), initiates an unusual oxidative skeletal rearrangement of the title cyclopentenone (I) in DMSO furnishing the lactone (III) as the major product. The expected epoxide (IV) can be obtained in poor yield under defined conditions. -(IVANOVA, N. A.; SHAINUROVA, A. M.; FURLEI, I. I.; MIFTAKHOV, M. S.; Izv.
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