• Bulletin of the Korean Chemical Society
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• v.19 no.9
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• pp.916-917
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• 1998

• Archives of Pharmacal Research
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• v.17 no.4
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• pp.249-255
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• 1994

An efficient synthetic method for 11-deoxyanthracycline AB synthons is described. A verstile key intemediate vinyl bromide 3 was prepared from 5- methodxy-1-tetralone in three steps, and then was converted to the allylic alcohols 4 and 8 which, in tum, fumished highly fuctionalized AB synthons 7 and 12, respectively, via sequential epoxidation-reduction-protection processes.

• Archives of Pharmacal Research
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• v.18 no.6
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• pp.458-461
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• 1995

+To prove uniqueness of allylic alcohol formation from ${\alpha},{\beta}-unsaturated$ ketones by mammal enzymes, a metabolic pattern of dehydroparadols, non-pungent synthetic analogs of shogaol by Aspergillus niger was examined. Two biotransformation products of a dehydroparadol, 1-(4hydroxy-3-methoxyphenyl)-non-1-en-3-one were accumulated in the culture broth of A. niger. They were characterized as 1-(4-hydroxy-3-methoxyphenyl)-non-1-en-9-01-3-one and 1-(4-hydroxy-3-methoxyphenyl)-nonan-9-o1-3-one by UV, NMR and mass spectroscopic analyses. Accumulation of allylic alcohol metabolites was not observed.

• Proceedings of the PSK Conference
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• 2003.10b
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• pp.179.1-179.1
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• 2003

Chiral building blocks have the importance in the pharmaceutical and agrochemical industries as well as in the development of rapid and efficient syntheses of bioactive compounds and natural product. Vinylstannane contains two synthetically useful functional groups (vinylstannane and allylic alcohol). The vinylstannane functional group can be used in C-C bond formation under a variety of conditions and the allylic alcohol functional can be used in hydroxyl-directed epoxidations, cyclopropanations, and sigmatropic rearrangements. (omitted)

• Archives of Pharmacal Research
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• v.5 no.2
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• pp.109-110
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• 1982

Conveersion of vinylogous glycidic ester 1 to 2 by a stereoselective acyclic allylic epoxidation will be presented.

• Bulletin of the Korean Chemical Society
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• v.25 no.1
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• pp.35-36
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• 2004

• Elastomers and Composites
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• v.55 no.1
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• pp.51-58
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• 2020

In this study, the thermal oxidation of raw natural rubber (NR) was investigated under controlled conditions by optical image and fourier transform infrared (FT-IR) analysis. The thermal oxidation was performed on a transparent thin film of raw NR coated on a KBr window in a dark chamber at 80℃ under low humidity conditions to completely exclude moisture and restrict light oxidation. Images of the thin film of raw NR were obtained before and after thermal oxidation. FT-IR absorption spectra were measured in the transmission mode at different thermal exposure times. The thermal oxidation of NR was examined by the changes in the absorption peaks at 3449, 1736, 1447, 1377, 1242, 1072, and 833 cm^-1, which corresponded to a hydroxyl group (-OH), a carbonyl group (-C=O) from an aldehyde and a ketone, a methylene group (-CH₂-), a methyl group (-CH₃), a carbon-oxygen single bond (-C-O) from an epoxide, a carbon-oxygen bond (-C-O) from an ether, an alcohol, a peroxide, or a cyclic peroxide, and a cis-methine group (cis-CCH₃=CH-), respectively. In the initial stage of thermal oxidation, two different types of free radicals were produced quickly and randomly by the homolytic cleavage of a double bond and allylic hydrogen abstraction. Aldehydes and ketones were formed from chain scissions of the double bonds and alcohols were produced from allylic hydrogen abstraction at the methylene or methyl groups. Two reactions seemed to proceed competitively with each other. At a later stage, oxidative crosslinks seemed to dominate through the combination of free radicals such as an allyl radical (CH=CHCH₂·), alkoxy radical (RO·), and peroxy radical (ROO·) and the reaction of a hydroperoxide (-ROOH) with a double bond. The image obtained after thermal oxidation showed hardening without cracks. Based on these observations, a plausible two-step mechanism was suggested for chain hardening caused by the thermal oxidation.

• Archives of Pharmacal Research
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• v.9 no.4
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• pp.237-242
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• 1986

The Synthesis of E, E, E-12-fluorofarnesol and E, Z-6-fluorofarnesol which are key intermediates for the study of biosynthesis of some sesquiterpenes, is described. E, E-Farnesyl acetate is treated with selenium dioxide to give E, E, E-12-hydroxy farnesyl acetate, whih is transformed by DAST into E, E, E-12-hydroxy farnesyl acetate, which is transformed by DAST into E, E, E,-12-fluorofarnesylacetate. The latter compound is hydrolyzed to E, E, E,-12-fluorofarnesol. The reformatsky reaction of 6-methyl-5-hepten-2-one with ethyl bromofluoroacetate affords ethyl 2-fluoro-3-hydroxy-3, 7 dimethyl-6-octanoate. This ester is acetylated and eliminated to give ethyl (Z)-2-fluoro-3, 7-dimethylocta-2, 6-dienoate, which is transformed to allyl bromide via allylic alcohol. The allyl bromide is treated with dianion of methyl acetate to give-keto ester. The $\beta$-keto ester is converted to diethyl phosphoryloxy compound. The conjugate addition of lithium dimethylcuprate to the latter compound gives fluoro ester, which is treated with DIBAL to afford E, Z-6-fluorofarnesol.

• Bulletin of the Korean Chemical Society
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• v.25 no.2
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• pp.221-225
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• 2004

A series of 2',3'-dideoxy-3'-fluoro-D-apiosyl nucleosides 15, 16, 17 and 18 were synthesized enantiomerically with L-Gulonic- ${\gamma}$-lactone as the starting material. The reduction of butenolide 1 with DIBAL-H followed by the Luche procedure afforded the allylic alcohol 2. Ozonolysis and the reduction of compound 4 induced the cyclized lactol, which was acetylated to give the acetate 7. Condensation of the acetate 7 with silylated pyrimidine ($N^4$-benzoyl cytosine) and a purine base (6-chloropurine) under Vorbruggen conditions and deblocking afforded a series of fluorinated apiosyl nucleosides.

• Journal of Integrative Natural Science
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• v.2 no.3
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• pp.185-189
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• 2009

The new MPV-type reagent, Al-fluorodiisobutylalane (DIBAF), has been prepared and their reducing characteristics in the reduction of selected organic compounds containing representative functional groups have been examined in order to find out a new reducing system with unique applicability in organic synthesis. In general, the reagent is extremely mild, showing only reactivity toward aldehydes, ketones, and epoxides. The reagent achives a clean 1,2-reduction of enals to the corresponding allylic alcohols in a 100% purity, but shows no reactivity toward enones. The reagent also shows an excellent regioselective cleavage of substituted epoxides. In addition, DIBAF produces the thermodynamically more stable alcohol epimer in high stereoselectivity in the reduction of cyclic ketones.