The total synthesis of the natural phenolic benzo[c]phenanthridine alkaloid, oxyterihanine, was accomplished via substituted 3-arylisoquinoline intermediate. The key reaction was a coupling between the o-toluamide 4 and the benzonitrile 5.
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https://www.riss.kr/link?id=A103905493
Thanh Nguyen Le (Chonnam National University) ; Hue Thi My Van (Chonnam National University) ; Suh-Hee Lee (Chonnam National University) ; 최현진 (전남대학교) ; 이광열 (전남대학교) ; 강복윤 (전남대학교) ; 조원제 (전남대학교)
2008
English
KCI등재,SCIE,SCOPUS
학술저널
6-9(4쪽)
8
0
상세조회0
다운로드다국어 초록 (Multilingual Abstract)
The total synthesis of the natural phenolic benzo[c]phenanthridine alkaloid, oxyterihanine, was accomplished via substituted 3-arylisoquinoline intermediate. The key reaction was a coupling between the o-toluamide 4 and the benzonitrile 5.
The total synthesis of the natural phenolic benzo[c]phenanthridine alkaloid, oxyterihanine, was accomplished via substituted 3-arylisoquinoline intermediate. The key reaction was a coupling between the o-toluamide 4 and the benzonitrile 5.
참고문헌 (Reference)
1 Le, T. N, "Total synthesis of oxyfagaronine, phenolic benzo[c]phenanthridine and general synthetic way of 2,3,7,8- and 2,3,8,9-tetrasubstituted benzo[c]phenanthridine alkaloids" 54 : 476-480, 2006
2 Simanek, V., "The Alkaloids" Academic Press 185-240, 1985
3 Le, T. N, "Synthesis of oxychelerythrine using lithiated toluamide-benzonitrile cycloaddition" 53 : 118-120, 2005
4 Ptaszek, M, "Synthesis of 1- formyldipyrromethanes" 71 : 4328-4331, 2006
5 Ishii, H, "Studies on the chemical constituents of rutaceous plants. LIX. The chemical constituents of Xanthoxylum nitidum (Roxb.) D.C. (Fagara nitida Roxb.) Examination of the alkaloidal fraction of the bark" 104 : 1030-1042, 1984
6 Ishii, H, "Studies on the Chemical-Constituents of Rutaceous Plants. 64. Structural Establishment of Oxyterihanine, a Phenolic Benzo[c]Phenanthridone Alkaloid - Syntheses of Phenolic Benzo[c]Phenanthridine Alkaloids, Terihanine and Isoterihanine, and Related-Compounds" 35 : 2717-2725, 1987
7 Nakanishi, T, "Structural considerations of NK109, an antitumor benzo[c]phenanthridine alkaloid" 62 : 864-, 1999
8 Nakanishi, T, "Revision of the structure of fagaridine based on the comparison of UV and NMR data of synthetic compounds" 61 : 1263-1267, 1998
9 Ishikawa, T, "Recent advances on antitumor-active benzo[c]phenanthridine alkaloids" 50 : 627-, 1999
10 Lista, L, "Practical one-pot conversion of 17-beta-estradiol to 10-betahydroxy-(p-quinol) and 10-beta-chloro-17-beta-hydroxyestra- 1,4-dien-3-one" 71 : 670-673, 2006
1 Le, T. N, "Total synthesis of oxyfagaronine, phenolic benzo[c]phenanthridine and general synthetic way of 2,3,7,8- and 2,3,8,9-tetrasubstituted benzo[c]phenanthridine alkaloids" 54 : 476-480, 2006
2 Simanek, V., "The Alkaloids" Academic Press 185-240, 1985
3 Le, T. N, "Synthesis of oxychelerythrine using lithiated toluamide-benzonitrile cycloaddition" 53 : 118-120, 2005
4 Ptaszek, M, "Synthesis of 1- formyldipyrromethanes" 71 : 4328-4331, 2006
5 Ishii, H, "Studies on the chemical constituents of rutaceous plants. LIX. The chemical constituents of Xanthoxylum nitidum (Roxb.) D.C. (Fagara nitida Roxb.) Examination of the alkaloidal fraction of the bark" 104 : 1030-1042, 1984
6 Ishii, H, "Studies on the Chemical-Constituents of Rutaceous Plants. 64. Structural Establishment of Oxyterihanine, a Phenolic Benzo[c]Phenanthridone Alkaloid - Syntheses of Phenolic Benzo[c]Phenanthridine Alkaloids, Terihanine and Isoterihanine, and Related-Compounds" 35 : 2717-2725, 1987
7 Nakanishi, T, "Structural considerations of NK109, an antitumor benzo[c]phenanthridine alkaloid" 62 : 864-, 1999
8 Nakanishi, T, "Revision of the structure of fagaridine based on the comparison of UV and NMR data of synthetic compounds" 61 : 1263-1267, 1998
9 Ishikawa, T, "Recent advances on antitumor-active benzo[c]phenanthridine alkaloids" 50 : 627-, 1999
10 Lista, L, "Practical one-pot conversion of 17-beta-estradiol to 10-betahydroxy-(p-quinol) and 10-beta-chloro-17-beta-hydroxyestra- 1,4-dien-3-one" 71 : 670-673, 2006
11 Mackay, S. P, "Advances in Heterocyclic Chemistry" 67 : 345-, 1997
12 Le, T. N, "A versatile total synthesis of benzo[c]phenanthridine and protoberberine alkaloids using lithiated toluamide-benzonitrile cycloaddition" 69 : 2768-2772, 2004
13 Le, T. N, "A facile synthesis of benzo [c]phenanthridine alkaloids: oxynitidine and oxysanguinarine using lithiated toluamide-benzonitrile cycloaddition" 45 : 2763-2766, 2004
14 Hanaoka, M, "A New Total Synthesis of Oxyterihanine" 26 : 1499-1501, 1987
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학술지 이력
연월일 | 이력구분 | 이력상세 | 등재구분 |
---|---|---|---|
2023 | 평가예정 | 해외DB학술지평가 신청대상 (해외등재 학술지 평가) | |
2020-01-01 | 평가 | 등재학술지 유지 (해외등재 학술지 평가) | |
2010-01-01 | 평가 | 등재학술지 유지 (등재유지) | |
2008-01-01 | 평가 | 등재학술지 유지 (등재유지) | |
2006-01-01 | 평가 | 등재학술지 유지 (등재유지) | |
2004-01-01 | 평가 | 등재학술지 유지 (등재유지) | |
2001-01-01 | 평가 | 등재학술지 선정 (등재후보2차) | |
1998-07-01 | 평가 | 등재후보학술지 선정 (신규평가) |
학술지 인용정보
기준연도 | WOS-KCI 통합IF(2년) | KCIF(2년) | KCIF(3년) |
---|---|---|---|
2016 | 1.96 | 0.2 | 1.44 |
KCIF(4년) | KCIF(5년) | 중심성지수(3년) | 즉시성지수 |
1.07 | 0.87 | 0.439 | 0.05 |