Chiral 7-Oxabicyclo[2.2.1]heptane Building Blocks for Prostanoids

Russian Journal of Organic Chemistry - Methyl (Z)-3-[(2R,3R,4S,5S)-5-(2-methoxy-2-oxoethyl)-3,4-(isopropylidenedioxy)tetrahydrofuran-2-yl]-prop-2-enoate was synthesized, and its intramolecular...     

β-Lactam Ring Opening in the Reformatsky Reaction of (3R,4R)-4-Acetoxy-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)azetidin-2-one with Ethyl 4-Bromo-3-oxopentanoate

Russian Journal of Organic Chemistry - The Reformatsky reaction of (3R,4R)-4-acetoxy-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)­azetidin-2-one with ethyl 4-bromo-3-oxopentanoate gave...     

Uncommon C1-C2 rupture in Methyl-4-C-allyl-2,4-dideoxy-3-O-mesyl-α-D-arabino-hexopyranoside

Russian Journal of Organic Chemistry -     

13C NMR spectra of biologically active compounds

The diastereomeric effects on the¹³C NMR chemical shifts of thirteen epimeric pairs of 16-aryloxy-11-deoxyprostaglandins of the E₁ and F₁ series caused by the change in the configuration of the 15-hydroxy group, which are differential parameters for assigning epimers to the 15- and 15-stereochemical series, have been determined.For Communication (VIII), see [1].Institute of Chemistry, Bashkir Scientific Center, Urals Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 123–128, January–February, 1991.     

Some features of RuCl3-catalyzed periodate oxidation of 3-N-substituted 5-allenyl-2,5-dichloro-4,4-dimethoxycyclopent-2-en-1-ones

3-N-Substituted 5-(1Z-carboxymethylene)-2-chloro-4,4-dimethoxycyclopent-2-en-1-ones have been prepared from the corresponding 3-N-substituted 5-allenyl-2,5-dichloro-4,4-dimethoxycyclopent-2-en-1-ones using selective oxidative cleavage of their allene bond by the RuCl₃−NaIO₄ system. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1646–1648, September, 1997.     

Prostanoids: XC. Extension to the Synthesis of Enprostil of the <Emphasis Type="Italic">o</Emphasis>-Nitrophenylsulfonylhydrazine Method for Transformation of 2-Propynyl Alcohols into Allenes

A potential precursor of enprostil, (±)-9-acetoxy-11,15-di-O-(tert-butyldimethylsilyl)-2-decarboxy-6-hydroxy-16-phenoxy-2-triphenylmethyloxymethyl-4,4,5,5-tetradehydro-17,18,19,20-tetranorprostaglandin F1α, was synthesized. This compound remained unchanged under the conditions for generation of allenes from 2-propynyl alcohols by the action of the system diisopropyl azodicarboxylate-triphenylphosphine-o-nitrophenylsulfonylhydrazine.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 7, 2005, pp. 988–994.Original Russian Text Copyright © 2005 by Vostrikov, Vasikov, Miftakhov.     

Prostanoids: LXXXVI. Synthesis and Reductive Transformations of 2-Chloro-4,4-ethylenedioxy-3-phenylsulfanyl-2-cyclopentenone

The reduction of 2-chloro-4,4-ethylenedioxy-3-phenylsulfanyl-2-cyclopentenone with sodium tetra-hydridoborate in ethanol yields 3-chloro-4-hydroxy-2-phenylsulfanyl-2-cyclopentenone, while with the use of lithium aluminum hydride in tetrahydrofuran or the system Zn/NH₄Cl in methanol products of more profound reduction are obtained.     

Reaction of 5-allyl-2,5-dichloro-4,4-dimethoxy-3-morpholinocyclopent-2-enone with Me3SiI

5-Allyl-2,5-dichloro-4,4-dimethoxy-3-morpholinocyclopent-2-enone reacts with Me₃SiI in MeCN to give the corresponding product of reductive vinylic monodechlorination. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1660–1661, August, 1998.