• Archives of Pharmacal Research
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• 제9권1호
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• pp.19-20
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• 1986

Reaction of dine alcohol 5 and maleic anhydride in benzene at either room temperature or reflux proceeds probably through a intermolecular Diels-Alder cycloaddition followed by lactone formation to give adduct 6.

• Bulletin of the Korean Chemical Society
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• 제7권3호
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• pp.166-169
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• 1986

In order to synthesize conformationally rigid etorphine analogues having potentially interesting pharmacological activities, synthesis of compound 3 by the reaction of compound 4 and compound 5 via intramolecular Diels-Alder reaction has been attempted. However, the reaction did not go well and the compound 3 would not be isolated. Therefore, intermolecular Diels-Alder reaction using dimethyl acetylene dicarboxylate was attempted. As shown in scheme 2, Diels-Alder adduct 9 was converted into the target molecule 14 containing the new [2.2.2] bicyclo octane ring in good yields.

• Bulletin of the Korean Chemical Society
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• 제32권spc8호
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• pp.2885-2886
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• 2011

• Bulletin of the Korean Chemical Society
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• 제10권2호
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• pp.129-132
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• 1989

Reactions of thebaine with phenylsulfonylpropadiene in various solvents were investigated. It was found that Diels-Alder reaction adduct was obtained in nonpolar solvent, while addition reaction adduct was obtained in polar solvent. Transformations of these two products were also carried out.

• Bulletin of the Korean Chemical Society
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• 제23권6호
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• pp.829-837
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• 2002

Recently it was reported that cycloaddition of 6,6-disubstituted cyclohexa-2,4-dienone, 1 with cyclopentadiene gave solely the adduct of type 1.while its reaction with 1,3-cyclohexadiene gave both Ⅱ and Ⅲ. Semiempirical MO calculations were done to elucidate the origin of the selectivity difference between the two dienes. Cycloaddition of 1 with cyclopentadiene is controlled thermodynamically to give only 1-diene adduct by ΔGvalues of 10.6-20.3 kcal/mol, while its reaction with 1,3-cyclohexadiene does not show 1-diene/1-dienophile selectivity due to similar stabilities of the two adducts. Thermodynamic parameters also show that 두애 adducts are more fabourably fromed in the cycloadditions of 1 with both cyclopentadiene and 1,3-cyclohexadiene, which coincides with experimental observations. Cope rearrangements of endo adducts are another avenue to convert between 1-diene and 1-dienophile.

• Bulletin of the Korean Chemical Society
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• 제19권9호
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• pp.957-961
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• 1998

Intramolecular Diels-Alder cycloadditions of 2-pyrone-3-carboxylates with trans-vinyl silaketal groups tethered via a chiral, non-racemic 1,3-butanediol auxiliary proceeded in unexpected stepwise cycloadditions through ionic intermediates to provide cis-disubstituted bicylolactones. The ratio of two isomers, exo and endo, was 5 to 1, and each isomer was found to be diastereomerically pure (>99% de). Their relative and absolute stereochemistries were determined by $^1H$ NMR spectroscopy and confirmed by X-ray crystallography of minor, endo-adduct 9. The major exo-adduct was successfully transformed to (-)-2-butyl substituted A-ring phophine oxide 16, a key element for the synthesis of 2-butyl vitamin D3.

• Bulletin of the Korean Chemical Society
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• 제8권5호
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• pp.376-380
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• 1987

The cyclobutane forming photocycloaddition reaction of 5(E)-styryl-1,3-dimethyluracil with some olefins occurs on the 5,6-double bond of uracil ring rather than the expected central double bond via an intermediate, probably the photochemical Diels-Alder type adduct. This intermediate formed on short term irradiation of 5(E)-styryl-1,3-dimethyluracil and 2,3-dimethyl-2-butene solution is converted into the $C_4$-cycloadduct on the prolonged irradiation. Quantum yield of the intermediate formation is not linear with the concentration of 2,3-dimethyl-2-butene probably due to the secondary reaction accompanied with the complex reaction kinetics. The intermediate is formed from the lowest excited singlet state.

• Journal of Applied Biological Chemistry
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• 제59권2호
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• pp.91-94
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• 2016

오디(Morus alba L.) 를 실온에서 80 % MeOH 수용액으로 추출하고 이 추출물을 EtOAc, n-butyl alcohol, 그리고 물 분획으로 나누었다. EtOAc 분획에 대하여 $SiO_2$ 및 ODS column chromatography를 반복 실시하여 2종의 Diels-Alder 부가화합물을 분리, 정제하였다. NMR, IR 및 ESI/MS data를 해석하여, 화합물 1과 2를 mulberrofuran E와 chalcomoracin 으로 각각 구조동정 하였다. 두 화합물 모두 오디로부터는 이번 실험에서 처음으로 분리되었다.

• Natural Product Sciences
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• 제25권3호
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• pp.233-237
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• 2019

Three Diels-Alder type adducts, guangsangon E (1), chalcomoracin (2) and sorocein I (3) were isolated from hairy root cultures of Morus macroura. The structures of the isolated compounds (1-3) were determined by spectroscopic method (NMR and MS), and spectral comparison to literature. Cytotoxic activities of the isolated compounds (1 - 3) were investigated against P-388 murine leukemia cell line. Guangsangon E (1) showed the most potent cytotoxicity against P-388 murine leukemia cell line with $IC_{50}$ value of $2.75{\pm}0.32{\mu}g/mL$. To the best of our knowledge, guangsangon E (1) and sorocein I (3) were reported for the first time from the tissue cultures of M. macroura.

• Bulletin of the Korean Chemical Society
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• 제33권10호
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• pp.3413-3416
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• 2012

Phenol-free resin was synthesized and its printing ink properties were investigated. The phenol-free resin was produced by esterification of poly phthalate and Diels-Alder adduct of rosin anhydride. Compared to rosin modified phenolic resin, eco-friendly phenol-free resin showed better vehicle properties in terms of gloss, yellowing, runability, and storage stability. The results suggest the utility of phenol-free resin instead of conventional rosin modified phenolic resin.