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RISS 인기검색어
- 검색키워드
- 저자 : Richard P. Rhee (검색결과 6 건)
- 무료
- 기관 내 무료
- 유료
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이풍래,노영쇠 全北大學校 1985 論文集 Vol.27 No.-
An efficient synthetic method for the regiospecific annelation of aromatic rings was developed. The efficacy of this ring annelation methodology was demonstrated by condensing an anion of phenylsulfonylisobenzofuranons(5), generated using LDA in THE at-76℃, with a Michael acceptor methyl trans-butenoate(7), which furnished, upon internal cyclization, a polyfunctionalized 1,4-disubstituted naphthalene 9 in a high yield. Preparation of 3-(phenylsulfonyl)-1(3H)-isobenzofuranone (5) was accomplished using methyl ο-toluate (1) as the starting material. Naphthalene 9 was converted to dimethyl ether 10 prior to final purification as the product was rather unstable in the air. The overall yield of naphthalene 10 from sulfone 5 was 86%.
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이풍래,노영쇠,최오곤 全北大學校 1985 論文集 Vol.27 No.-
4-Methoxy-3-methylphenol, a key compound for the total synthesis of Antitumor antibiotic Nogalamycin was successively prepared. The target molecule was synthesized via six step reaction sequence by transforming three individual functional groups present in the srarting compound, 2,5-dihydroxybenzoic acid. Thus, the carboxyl function of 2,5-dihydroxybenzoic acid was first esterified to give a methyl ester and then the phenolic hydroxyl groups at C-5 and C-2 were transformed into benzyl and methyl ethers, repectively. After reducing the ester function of methyl benzoate, the resulting benzyl alcohol was converted to a tosylate. The tosylate function was then reduced to a methyl group using metal hydride. The remaining benzyloxy group at C-5 was finally deprotected by catalytic hydrogenation to furnish 4-methoxy-3-methylphenol.
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항암항생제 Daunorubicin의 Aglycone, 7,9-Dideoxydaunomycinone의 합성 (제1보)
조인호,이풍래,노영쇠,In Ho Cho,Richard P. Rhee,Young Soy Rho,F. M. Hauser 대한화학회 1986 대한화학회지 Vol.30 No.1
항암항생제 Daunorubicin(2a)합성단계의 최종물질인 7,9-Dideoxydaunomycinone (32)를 3-methoxybenzoic acid(5)로 부터 합성하였다. 3-methoxybenzoic acid를 4-methoxy-3-(phenylsulfonyl)-1(3H)-isobenzofuranone(11)으로 변형시킨 뒤 Hauser와 Rhee가 개발한 고리접합법을 이용하여 trimethoxynaphthoate 16을 얻은 후에 phenylsulfonylnaphthofuranone 22로 변화시킨 뒤 이 물질을 7-(ethylenedioxy)-2-octenoate(23)과 Michael형태의 반응을 전개시켜 anthracenoate 24를 얻었다. Anthracenoate을 tetracyclic 화합물 28로 바꾼뒤 ring B와 C에 붙은 methyl기들을 제거하여 7,9-Dideoxydaunomycinone(32)를 만들었다. 7,9-Dideoxydaunomycinone (32), a late-stage precursor of the aglycone of antitumor antibiotic daunorubicin(2a) was prepared from 3-methoxybenzoic acid(5). Thus, 3-methoxybenzoic acid was converted to 4-methoxy-3-(phenylsulfonyl)-1(3H)-isobenzofuranone(11), which furnished trimethoxynaphthoate 16 upon ring annelation developed by Hauser and Rhee. The trimethoxynaphthoate 16 upon ring annelation developed by Hauser and Rbee. The trimethoxynaphtboate 16 was then transformed into phenylsulfonylnaphthofuranone 22, which was used to make anthracenoate 24 via Michael type reaction with 7-(ethylenedioxy)-2-octenoate(23). Conversion of anthracenoate 24 to tetracyclic product 28, followed by subsequent deprotection of the methyl groups in ring-B and C furnished 7, 9-Dideoxydaunomycinone(32).
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항암항생제 Rhodomycin의 Aglyconed인 (±)-γ-Rhodomycinone과 10-Deoxy-γ-rhodomycinone의 합성(제2보)
趙仁鎬,전진순,魯永釗,Rhee, Richard P 全北大學校 基礎科學硏究所 1991 基礎科學 Vol.14 No.1
항암항생제 Rhodomycin(2)의 합성단계 최종물질인 (±)-γ-Rhodomycinone(4)과 10-Deoxy-γ-rhodomycinone(5)이 9-ethyl-9,10-epoxy-4,6,11-trihydroxy-7,8,9,10-tetrahydronaphthacene-5,12-dione(10)의 epoxide ring 쪼개짐으로부터 만들어졌고, epoxide 10은 Hauser-Rhee가 개발한 고리접합법을 이용해서 만든 9-acetyl-4,5,6,11,12-pentamethoxy-7,8-dihydronaphthacene(6)으로 부터 얻었다. (±)-γ-Rhodomycinone(4) and 10-Deoxy-γ-rhodomycinone(5), late-stage Precursors of the alglycone of antitumor antibiotic Rhodomycin(2) were prepared from the cleavage of epoxide ring of 9-ethyl-9,10-epoxy-4,6,11-trihydroxy-7,8,9,10-tetrahydronaphthacene-5,12-dione(10). The epoxide 10 was furnished from 9-acetyl-4,5,6,11,12-pentamethoxy-7,8-dihydronaphthacene(6), which was assembled utilizing ring annelation methodology developed by Hauser-Rhee.
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조인호,이풍래,노영쇠 全北大學校 基礎科學硏究所 1983 基礎科學 Vol.6 No.1
A brief, efficient aromatic ring annelation method was developed. The new ring annelation methodology involves condensation of the anion of 3-phenylsulfonyl-1(3H)-isobenzofuranone with Michael acceptor, methyl crotonate to give a initial adduct. The resulting adduct is then in situcyclized and aromatized to furnish regiospecifically constructed, selectively protected 1,4-dimethoxy-2,3-disubstituted naphthalene, after methylation of the resulting product. This new ring annelation method provides an efficient, reginspecific synthetic route for the polynuclear aromatic systems which constitutes the key structural portion of various important polynuclear aromatic antitumor antibiotics.
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조인호,정진순,노영쇠,In Ho Cho,Jin Soon Chung,Young S. Rho,Richard P. Rhee 대한화학회 1988 대한화학회지 Vol.32 No.6
항암항생제 Rhodomycin(2)의 합성단계 최종물질인 (${\pm}$)-${\gamma}$-Rhodomycinone(4) 과 10-Deoxy-${\gamma}$-rhodomycinone(5)이 9-ethyl-9,10-epoxy-4,6, 11-trihydroxy-7,8,9,10-tetrahydronaphthacene-5,12-dione(10)의 epoxide ring 쪼개짐으로부터 만들어졌고, epoxide 10은 Hauser-Rhee가 개발한 고리접합법을 이용해서 만든 9-acetyl-4,5,6,11,12-pentamethoxy-7,8-dihydronaphthacene(6)으로 부터 얻었다. $({\pm})-{\gamma}$-Rhodomycinone(4) and 10-Deoxy-${\gamma}$-rhodomycinone(5), late-stage Precursors of the alglycone of antitumor antibiotic Rhodomycin(2) were prepared from the cleavage of epoxide ring of 9-ethyl-9,10-epoxy-4,6, 11-trihydroxy-7,8,9,10-tetrahydronaphthacene-5,12-dione(10). The epoxide 10 was furnished from 9-acetyl-4,5,6,11,12-pentamethoxy-7,8-dihydronaphthacene(6), which was assembled utilizing ring annelation methodology developed by Hauser-Rhee.
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