T. A. Belogaeva

Prostanoids: LXXXII. Synthesis of Key Precursors of 9-LO Thromboxans

Starting from levoglucosan, methyl 2,4-dideoxy-3-O-mesyl-4-C-[(2Z)-octenyl]-α-D-arabino-hexopyranoside and (+)-2α-methoxy-6β-[6-methoxycarbonyl-3-oxo-(1E)-hexenyl]-5α-[(2Z)-octenyl]pyran-3-one were synthesized as potential building blocks for preparation of 9-LO thromboxanes.

Prostanoids: LXXXI. Synthesis of (±)-2-Decarboxy-2-ethyl-19,20-dinor-18-carboxyprostaglandin E1

Abstract2-Decarboxy-2-ethyl-19,20-dinor-18-carboxyprostaglandin E1 was synthesized starting from (±)-7α-hydroxy-6β-hydroxymethyl-2-oxa-cis-bicyclo[3.3.0]octan-3-one.

CHROMIUM(II) CHLORIDE AS A HIGHLY SELECTIVE C(5)-DECHLORINATING AGENT FOR FUNCTIONALIZED 2,3,5-TRICHLOROCYCLOPENT-2-EN-1-ONES

Abstract(±)-2,3,5-Trichloro-4,4-ethylenedioxy- and (±)-5-allyl(allenyl)-2,3,5-trichloro-4,4-dimethoxycyclopent-2-en-1-ones undergo regioselective reductive C(5)-dechlorination under the action of CrCl2 to give the corresponding 2,3-dichlorocyclopentenones.

Prostanoids: LXXXV. Synthesis 9-Oxo Derivatives of 9-LO Thromboxans

Starting from levoglucosan, 1,6-anhydro-2,4-dideoxy-4-C-(2Z-octenyl)-β-D-arabino-hexopyranose was synthesized and converted into 9-oxo-9-LO thromboxan δ-lactone.

A novel variant for the preparation of allyl(propargyl) vinyl ethers and their rearrangement into 5-allyl(allenyl)-5-chloro-2-(2-hydroxyethyloxy)-cyclopent-2-ene-1,4-diones

Reactions of 1,2-di- and 1,2,4-trichloro-6,9-dioxaspiro[4.4]non-1-en-3-ones with sodium 2-propenoxide or sodium 2-propynoxide afforded the corresponding 3-allyloxy or 3-propynyloxycyclopentenones, as well as the products of their subsequent thermal [3,3]-sigmatropic rearrangement.

Prostanoids: LXXXVIII. Chlorocyclopentenone Building Blocks in the Synthesis of Marine Prostanoids

Starting from 2,3-dichloro-4,4-ethylenedioxy-2-cyclopentenone, a practical procedure has been developed for the synthesis of a series of 4-substituted 2-chloro-4-hydroxycyclopentenones.

Prostanoids: LXXXIII. Synthesis of (′)-19-carboxy-20-norprostaglandin F2α and its 15β-epimer

Starting with (±)-7α-hydroxy-6β-hydroxymethyl-2-oxa-cis-bicyclo[3.3.0]octan-3-one 15α,β-19-carboxy-20-norprostaglandins Fα were synthesized.

Reactions of (Me2N)3P with functionalized di- and trichlorocyclopentenones

Abstract2,3-Dichloro-4,4-ethylenedioxycyclopent-2-enone, its 5-chloroderivative, and 5-allyl-2,3,5-trichloro-4,4-dimethoxycyclopent-2-enone react with (Me2N)3P to give the corresponding products of substitution of the NMe2 group for the vinylic Cl atom at C(3).

(±)-2,3,5-trichloro-4,4-ethylenedioxycyclopent-2-en-1-one and its 5-allyl-substituted derivative in conjugated 1,4-addition with dimethyldilithium cyanocuprate

Abstract(±)-2,3,5-Trichloro-4,4-ethylenedioxycyclopent-2-en-1-one reacts with Me2CuCNLi2 to give depending on conditions the corresponding 3-methyl substituted cyclopentenone (AdNE adduct) or a mixture of unsaturated acyclic 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 Me2CuCNLi2 to (±)-5-allyl-2,3,5-trichloto-4,4-dimethoxycyclopent-2-en-1-one lead to products of replacement of vinylic Cl atom at C(3) by Me group and those of C(5)-dechlorination.