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Michael 반응을 이용한 Naphthacenone 유도체의 합성
노영쇠,유진호,박시호,조인호,권윤자,Rho, Young S.,Yoo, Jin H.,Park, Si H.,Cho, In H.,Kwon, Yoon J. 대한화학회 1996 대한화학회지 Vol.40 No.7
3-Carbomethoxy-1(3H)-isobenzofuraneme(9)과 .alpha., .beta.-불포화 에스테르 화합물 3a-b를 각각 반응시켜서 naphthacene-6, 7-dione 11a-b를 좋은 수율로 얻었다. 이들 중 C-9 위치에 에틸기가 없는 11a는 산화시켰을 때 naphthacene-5, 12-dione 13a가 생성되는 반면, 에틸기를 갖고 있는 11b는 naphthacene-5, 7, 12-trione 12b와 naphthacene-5, 12-dione 13b가 3:2로 생성되어졌다. 3-Carbomethoxy-1(3H)-isobenzofuranone(9) underwent condensation with ${\alpha}{\beta}-unsaturated$, esters 3a-b to produce the corresponding naphthacene-6,7-diones 11a-b with high yields in one pot procedure. Among the naphthacene-6,7-diones formed, compound 11a without an ethyl group at C-9 position was oxidized to give the naphthacene-5,12-dione 13a, while compound 11b containing the ethyl group was oxidized to give a 3:2 mixture of the naphthacene-5,7,12-trione 12b and naphthacene-5,12-dione 13b under the same experimental conditions.
항암항생제 11-Deoxy-beta-rhodomycinone의 합성
노영쇠(Young S. Rho),강혼수(Heun Soo Kang),신홍식(Hong Sig Sin) 대한약학회 1993 약학회지 Vol.37 No.6
Methyl 3-[(phenylsulfonyl)methyl]-1,4,8-trimethoxy-2-naphthoate(7) preparad by 3 steps was condensed with 5-ethyl-2-cyclohexen-l-one(8) to afford the teracyclic aromatic ring system compound 10, which was stepwise converted into the precursor of 11-Deoxy-beta-rhodomycinone by means of various functional groups transformation.
노영쇠(Young S. Rho),김선자(Sun Ja Kim),조인호(In Ho Cho),신홍식(Hong Sig Sin) 대한약학회 1999 약학회지 Vol.43 No.1
A brief route for regiospecific synthesis of novel 10-oxodaunomycinone derivatives (10a, b) is described. Dimethoxy-1-tetralone 4 was converted to acetyl tetralone (5a, b) which was oxidized with oxygen to obtain cis-diol compound (8a, b). The construction of (10a, b) was completed by the condensation of phthaloyl dichloride 9 with cis-diol (8a, b).
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.
항암항생제 11-Deoxy-β-rhodomycinone 의 합성
노영쇠,강혼수,신홍식 全北大學校 基礎科學硏究所 1994 基礎科學 Vol.16 No.-
Methyl 3-[(phenylsulfonyl)methyl]-1,4,8-trimethoxy-2-naphthoate(7) preparad by 3 steps was condensed with 5-ethyl-2-cyclohexen-1-one(8) to afford the teracyclic aromatic ring system compound 10, which was stepwise converted into the precursor of 11-Deoxy-β-rhodomycinone by means of various functional groups transformation.
趙仁鎬,韓秉九,柳東辰,李準龍,魯永釗 全北大學校 1990 論文集 Vol.32 No.-
A regiospecific synthesis of 9-alkyltetracyclinone derivatives are described. Methoxybenzoylchloride was transformed to methoxy-3-(phenylsulfonyl)-1(3H)-isobenzofuranone 1a 1b which was converted to an anion and condensed with 6-ethyl-4a,7,8,8a-tetrahydro-1(4H)-naphthalenone(2) to afford 4-methoxy-6-hydroxy-9-ethyl-7,8-dihydronaphthacene-5,12-dione(4a) and 1-methoxy compound(4b) after oxidation. The double bonds of 4 were hydroxylated with osmium tetroxide to afford cis 9-ethyl-4(or 1)-methoxy-6,9,10-trihydroxy-7,8,9,10-tetrahydronaphthacene-5,12-dione(7). For the purpose of studies of spectroscopic difference for trans 8 and cis diol 7, compound 4 was transformed to 9,10-epoxy-9-ethyl-6-hydroxy-4(or 1)-methoxy-7,8,9,10-tetrahydronaphthacene-5,12-dione(5) which was hydroxylated with 4N sulfuric acid to afford trans compound 8.
Hauser, Frank M,Hewawasam, Piyasenan,Rho, Young S 全北大學校 基礎科學硏究所 1991 基礎科學 Vol.14 No.1
A brief route for total synthesis of(±)-aklavinone(1a), the aglycon of the anticancer antibiotic aclacinomycin(1b), is described. Key features of the synthesis are the development of a brief, efficient route to the 1(4H)-naphthalenone 1l, which was used as a synthon for the A and B rings, and homologation of keto aldehyde 17 to the keto anthraquinone acetic ester 16 via the intermediacy of the ketene thioacetal 19.
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.
Stereisoecific Syntheses of (E)-1,3-Disubstituted Dienes
Hauser, Frank M.,Tommasi, Ruben,Hewawasam, Piyasena,Rho, Young S. 全北大學校 基礎科學硏究所 1999 基礎科學 Vol.14 No.1
In summary, the palladium-catalyzed conversion of allylacetates with a 2-alkyl group on the vinyl moiety provides a general, high-yield route for selective syntheses of E isomers of 1,3-disubstituted dienes. The reaction conditions are mild and compatible with a variety of functional groups elsewhere in the molecule. Currently, we are ap-plying these results to other synthetic work, which will be reported shortly.