Medium ring compounds. VII. Synthesis of 2-methyl-7-oxoundecanolide, 8-oxoundecanolide, and 2,4,6-trimethyl-7-oxodecanolide

Abstract

.-To a suspension of 1,3-dibenzyl-6-aminouracil (3.07 g, 10 mmol) in 20 ml of DMF was added dimethyl acetylenedicarboxylate (1.56 g, 11 mmol) and the mixture was heated at 110°f or 2 hr. To the dark red solution was added 150 ml of ether. The resulting precipitate was filtered and washed with 40 ml of ether to yield 1.62 g (39%), mp 235°. Recrystallization of a 1.1-g sample from DMF-HjO gave 0.9 g: mp 239-240°u v (pH 1) 438 nm (e 5500), 336 (6850), 270 (15,830), (pH 7) 330 (22,400), 273 (7930), (pH 11) 330 (22,100), 273 (7930);

The Glutamate Receptor GluR5 Agonist (S)-2-Amino-3-(3-hydroxy-7,8-dihydro-6H-cyclohepta[d]isoxazol-4-yl)propionic Acid and the 8-Methyl Analogue: Synthesis, Molecular Pharmacology, and Biostructural Characterization†PDB ID: 2WKY.

“…The new synthetic route to 4 (Scheme ) commenced like previously reported syntheses from O -alkyl ketone 9a , , which was prepared from ethyl 2-oxoheptanecarboxylate 6a in three steps via 7a and 8a . Similarly, the methylated analogue 9b could be synthesized from ethyl ( RS )-3-methyl-2-oxoheptanecarboxylate 6b via 7b and 8b . Treatment of ketones 9a and 9b with hydrazine gave the hydrazones 10a and 10b in 97% and 89% yield, respectively.…”

“…(RS)-8-Methyl-5,6,7,8-tetrahydro-4H-cyclohepta[d ]isoxazol-3-ol (7b). A solution of ethyl 3-methyl-2-oxoheptanecarboxylate (6b) 27 (2.07 g, 10.4 mmol) in MeOH (2 mL) was carefully added to NaOH (437 mg, 10.9 mmol) dissolved in MeOH (7 mL) and H 2 O (0.5 mL) at -70 °C. To this solution was added a mixture of NH 2 OH 3 HCl (1.45 g, 21 mmol) and NaOH (0.87 g, 22 mmol) in MeOH (8 mL) and H 2 O (1 mL) filtered and precooled to -70 °C.…”

Peptidomimetic Inhibitors of Herpes Simplex Virus Ribonucleotide Reductase with Improved in Vivo Antiviral Activity

“…The preparations of Boc-2( S )-amino-4-pyrrolidino-4-oxobutanoic acid (pyrrolidine modified asparagine moiety) 8 , N -Boc- l -γ-methylleucine, and the appropriately protected precursor of cyclopentylaspartic acid 9 have been described in our earlier structure−activity papers. The various stereochemically defined 2,6-dimethylcyclohexylamines were prepared from 2,6-dimethylphenol according to the procedures in refs and . The enantioselective synthesis of 2( R )- or 2( S )-ethyl/methyl-3,3-dimethylpropylamine has been published …”

Synthetic studies on terpenoids. 5. Synthesis of .gamma.- and .delta.-lactones from .beta.-(2,7-dimethyl-1,2-dihydroxycycloheptyl)propionic acid

“…This was also prepared through the fission of ethyl 2-methylcycloheptanone-2-carboxylate in the presence of a catalytic amount of sodium ethoxide. 10 The diester was subjected to cyclization according to modified high-dilution technique.11 The cyclized product was methylated in situ to afford 2-ethoxycarbonyl-2-7-dimethylcycloheptanone and this on hydrolysis gave 2,7-dimethylcycloheptanone. The ketone was found by GC analysis to be a mixture (4:1) of two components.…”