Synthesis of enantiomerically pure macrolides with hydrazide fragments from tetrahydropyran and l-(+)-tartaric acid derivatives

Synthesis of Macrolides with Hydrazide Fragments from Tetrahydropyran and 2,6-Pyridinedicarboxylic Acid

“…The synthesis of two potentially biologically and pharmacologically active 23-and 29-membered macrolides Reagent: i) [3];ii) [4]; iii) [5]; iv) , 1,4-dioxane, 37%, 35%.…”

“…[1,2] Their [1+1]-condensation with hydrazine hydrate or dihydrazides of malonic, glutaric, adipic, [1,2] azelaic, sebacic, 7-oxabicyclo[2.2.1]heptenoic [3] and tartaric [4,5] acids led to macroheterocycles containing one or two ester groups and azine or dihydrazide fragments. One of the synthesized macrolides 4 showed a significant (at the level of erythromycin) antibacterial activity in vitro and in vivo against the museum and field strains of pathogenic microorganisms (Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa).…”

Reactions of bicyclo[2.2.1]heptane-2-endo,3-endo-dicarbohydrazide and its 5-endo,6-endo- and 5-endo,6-exo-dihydroxy derivatives with 7-oxooctyl 7-oxooctanoate and bis(7-oxooctyl) hexanedioate

“…Macrolides with nitrogen-containing (azine or hydrazide) fragments are commonly prepared by the Tishchenko disproportionation of ketoaldehydes to α,ω-diketo esters or [2 + 1]-condensation of hydroxy esters with α,ω-dicarboxylic acid dichlorides and subsequent macrocyclization by the action of an equimolar amount of hydrazine hydrate or α,ω-dicarboxylic acid hydrazides [1][2][3][4][5][6][7][8][9].…”

“…Starting from tetrahydropyran (1), we previously synthesized diketo ester 2 and diketo diester 3 and used them in the synthesis of nitrogen-containing macroheterocycles [1,[7][8][9][10]. Herein we report the transformations of compounds 2 and 3 in reactions with bicyclo[2.2.1]heptane-2-endo,3-endo-dicarbohydrazide (5) and its 5-endo,6-endo-and 5-endo,6-exodihydroxy derivatives 6a and 6b which were prepared DOI: 10.1134/S1070428015060020 Scheme 1.…”

Interaction of 7-oxoоctyl-7-oxooctanoate and bis(7-oxooctyl)hexandioate with phthalic dihydrazide

“…We have already reported [1][2][3][4][5][6][7][8][9] on the synthesis of a whole range of macroheteroсycles with ester, azyne and hydrazide fragments using key α,ω-diketones (2, 3) available, in turn, from tetrahydropyran. [2,10] This report considers an unusual cyclization reaction of diketo diester (2) and diketo ester (3) under the influence of phthalic dihydrazide (4).…”