Ya. M. Katok

Heterocyclic Analogs of Prostaglandins: I. Synthesis of 3-Alkyl(Aralkyl)-2,5-dihydrofuran-2-ones as Synthons for 11-Deoxy-10-oxaprostanoids

Abstract3-Acyl(arylmethyleneacyl)tetronic acids were synthesized. Selective hydrogenation of the carbonyl group in the acyl fragment and reduction of the conjugated double bond afforded in high yield the corresponding 3-alkyl(aralkyl) derivatives possessing either natural or modified prostaglandin α-chain. Reduction of the conjugated double bond in vinylogous 3-alkyl(aralkyl)tetronic acid amides with sodium cyanotrihydridoborate gave a mixture of stereoisomeric β-amino lactones which underwent retro-Michael elimination of the amine residue, leading to 3-alkyl(aralkyl)-2,5-dihydrofuran-2-ones. The latter can be regarded as synthons for 11-deoxy-10-oxaprostanoids.

Heterocyclic analogs of prostaglandins: II. Synthesis of 10-oxaprostanoids with isoxazole and isoxazoline fragments in α-and ω-chain

By the use of “nitrile oxide procedure” from 3-alkyl(arylalkyl)-substituted 2,5-dihydro-2-furanones new 10-oxaprostanoids were prepared containing an isoxazole (isoxazoline) fragment in the α-or ω-prostanoid chain.

Reaction of 3,5-disubstituted 4,5-dihydroisoxazoles with hexacarbonylmolybdenum

Depending on the reaction conditions and structure of the 5-substituent, reactions of substituted 4,5-dihydroisoxazoles with hexacarbonylmolybdenum involve cleavage of the heteroring at the N-O bond, its aromatization, or/and 1,3-decyclization.

Synthesis and Reductive Transformations of 11-Deoxyprostanoids with a 4,5,6,6a-Tetrahydro-3aH-cyclopenta[d]isoxazole Fragment in the ω-Chain

A new prostanoid precursor with a 4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole fragment in the ω-chain was synthesized using the nitrile oxide technique. Its reduction afforded new 11-deoxyprostanoids with modified α- and ω-chains.