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The Stereospecific Synthesis of Abscisic Acid
Oee-Sook Park,W. Y. Lee,J. C. Park 한국생약학회 1986 생약학회지 Vol.17 No.1
A stereospecific synthesis of 3-methyl-5-(1-hydroxy-4-oxo-2, 6, 6-trimethyl-2-cyclohexen-1-yl)-cis, trans-2, 4-pentadienoic acid (abscisic acid) from a-ionone has been investigated. Ethyl 5-(2, 6, 6-trimetyl-2-cyclohexen-1-yl)-trans-4-penten-2-ynoate (α, β-acetylenic ester), which was synthesized from α-ionone in two steps, was stereospecifically converted in good yield into ethyl 3-methyl-5-(2, 6, 6-trimethyl-2-cyclohexen-1-yl)-cis, traps-2, 4-pentadienoate (α-ionylideneacetate) by the conjugate addition of lithium dimethylcuprate at -78C. Basic hydrolysis of the ethyl α-ionylideneacetate gave an abscisic acid precursor, 3-methyl-5-(2, 6, 6-trimethyl-2-cyclohexen-1-yl)-cis, traps-2, 4-pentadienoic acid, which can be oxidized to yield abscisic acid.
A New Synthesis of 6,10,14,18-Tetramethyl-5,9,13,17 (E,E,E)-nonadecatetraen-2-one
Park, Oee-Sook,Ahn, Su-Kyung The Pharmaceutical Society of Korea 1993 Archives of Pharmacal Research Vol.16 No.4
6, 10, 14, 18-Tetramethyl-5, 9, 131, 17(E, E, E)-nonadecatetraen-2-one was synthesized from geraniol or 6-methyl-5(E)-hepten-2-one in 6 steps, repectively. The key step in both syntheses, was the condensation of phenyl sulfone compound and allylic chloride.
A New Synthesis of ($\pm$)-Myodesmone
Park, Oee-Sook,Hwang, Hyun-Joo,Lee, Woo-Young The Pharmaceutical Society of Korea 1993 Archives of Pharmacal Research Vol.16 No.3
($\pm$)-Myodesmone was synthesized, starting from 2-cyclopentenone. The key reaction involved $\alpha$-dimethoxymethylation of 2-cyclopentenone and organocopper conjugate addition reaction.
Park, Oee-Sook,Lim, Jae-Gyeong The Pharmaceutical Society of Korea 1996 Archives of Pharmacal Research Vol.19 No.6
A new formal total synthesis of (+)-6-oxo-3, 4, 4a, 5-tetrahydro-3-hydroxy-2, 2-dimenthylnaphtho-1, 2-pyran (1) which has been known to have bactericidal, bacteriostatic, fungicidal, fungistatic activities against Staphylococcus aureus and other microorganism, is described. The key reaction involves enantioselective prenylation of .alpha.-tetralone via chiral lithioenamine.
Synthesis of 4-Hydroxycoumarion Derivatives-1: An Efficient Synthesis of Flocoumafen
Park, Oee-Sook,Jang, Bong-Suek The Pharmaceutical Society of Korea 1995 Archives of Pharmacal Research Vol.18 No.4
An anticoagulant, 4-hydroxy-3-[1, 2, 3, 4-tetrahydro-3-[4-(4-trifluoromethylbenzyloxy)phenyll-1 -naphthyl]coumarin (Flocoumafen) was synthesized in 8 steps starting from phenylacetyl shloride and anisole. The key step in the synthesis involves the reaction of 3-(4-methoxyphenyl)-1-teralol with 4-hydroxycoumarin to give 4-hydroxy-3 [1, 2, 3, 4-tetrahydro-3-[4-emthoxyphenyl]-1-naphthyl]coumarin.
Studies on the Synthesis of Naphthoquinoids
Park, Oee-Sook,Kim, Ju-Cheun The Pharmaceutical Society of Korea 1998 Archives of Pharmacal Research Vol.21 No.3
Four derivatives of 6-oxo-3,4,4a,5-tetrahydro-3-hydroxy-2,2-dimethylnaphtho-1,2-pyran (1), known as bacterial, bacteriostatic, fungicidal, fungistatic agents, were synthesized to investigate the effect of substituents on the aromatic ring.
Isolation of Solanesol from Korean Native Tobacco
Oee-Sook Park(박외숙) 한국생약학회 1981 생약학회지 Vol.12 No.4
Solanesol has been isolated from aged Korean native tobacco leaf(Hyangcho and Sohyang) by water pretreatment, hexane extraction and column chromatography on Florisil in yields of 0.41% and 0.31% dry wt., respectively. Thin-layer densitometric analysis of the hexane extracts of samples(Hyangcho Sohyang) has shown that the amounts of solanesol present are 0.74% and 0.52% dry wt., respectively.
Park, Oee-Sook,Son, Hoe-Joo,Lee, Woo-Young The Pharmaceutical Society of Korea 1987 Archives of Pharmacal Research Vol.10 No.4
An efficient and inexpensive method for the substitution of allylic hydroxyl group with fluoride, without allylic rearrangement, and elimination was developed. This method consists of treating an allylic alcohol with methylithium, followed by p-toluene sulfonyl fluoride, lithium fluoride and 12-Crown-4. This methodology was proved to be efficient by preparting geranyl fluoride, neryl fluoride, cinnamyl fluoride, E, E-farnesyl fluoride, retinyl fluoride and 4-fluoro-2-methyl-6-(ptolyl)-2-heptene.