메뉴 건너뛰기




Volumn 72, Issue 8, 2008, Pages 2092-2102

Regioselectivity of larock indole synthesis using functionalized alkynes

Author keywords

Acetylene; Indole; Larock indole synthesis; Palladium; Regioselectivity

Indexed keywords

AMINES; ESTERS; FUNCTIONAL GROUPS; GLUCOSE; HYDROCARBONS; OPTICAL SENSORS; ORGANIC COMPOUNDS; PALLADIUM; REGIOSELECTIVITY;

EID: 51049101659     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.80179     Document Type: Article
Times cited : (9)

References (23)
  • 1
    • 0000428035 scopus 로고
    • Synthesis of indoles via palladium-catalyzed heteroannulation of internal alkynes
    • Larock, R. C., and Yum, E. K., Synthesis of indoles via palladium-catalyzed heteroannulation of internal alkynes. J. Am. Chem. Soc., 113, 6689-6690 (1991).
    • (1991) J. Am. Chem. Soc , vol.113 , pp. 6689-6690
    • Larock, R.C.1    Yum, E.K.2
  • 2
    • 33744870975 scopus 로고    scopus 로고
    • Synthesis of 2,3-disubstituted indoles via palladium-catalyzed annulation of internal alkynes
    • Larock, R. C., Yum, E. K., and Refvik, M. D., Synthesis of 2,3-disubstituted indoles via palladium-catalyzed annulation of internal alkynes. J. Org. Chem., 63, 7652-7662 (1998).
    • (1998) J. Org. Chem , vol.63 , pp. 7652-7662
    • Larock, R.C.1    Yum, E.K.2    Refvik, M.D.3
  • 4
    • 0035967767 scopus 로고    scopus 로고
    • Efficient asymmetric synthesis of biologically important tryptophan analogues via a palladium-mediated heteroannulation reaction
    • Ma, C., Liu, X., Li, X., Flippen-Anderson, J., Yu, S., and Cook, J. M., Efficient asymmetric synthesis of biologically important tryptophan analogues via a palladium-mediated heteroannulation reaction. J. Org. Chem., 66, 4525-4542 (2001).
    • (2001) J. Org. Chem , vol.66 , pp. 4525-4542
    • Ma, C.1    Liu, X.2    Li, X.3    Flippen-Anderson, J.4    Yu, S.5    Cook, J.M.6
  • 5
    • 0842306887 scopus 로고    scopus 로고
    • a-methylvellosimine, (+)-12-methoxyaffinisine, and (-)-fuchsiaefoline
    • a-methylvellosimine, (+)-12-methoxyaffinisine, and (-)-fuchsiaefoline. Org. Lett., 6, 249-252 (2004).
    • (2004) Org. Lett , vol.6 , pp. 249-252
    • Zhou, H.1    Liao, X.2    Cook, J.M.3
  • 6
    • 19944400088 scopus 로고    scopus 로고
    • Synthesis of (±)-lotthanongine, a novel natural product with a flavan-indole hybrid structure
    • Hatakeyama, K., Ohmori, K., and Suzuki, K., Synthesis of (±)-lotthanongine, a novel natural product with a flavan-indole hybrid structure. Synlett, 1311-1315 (2005).
    • (2005) Synlett , vol.1311-1315
    • Hatakeyama, K.1    Ohmori, K.2    Suzuki, K.3
  • 7
    • 0032911810 scopus 로고    scopus 로고
    • Synthesis of a α-C-mannosyltryptophan derivative, naturally occurring C-glycosyl amino acid found in human ribonuclease
    • Nishikawa, T., Ishikawa, M., and Isobe, M., Synthesis of a α-C-mannosyltryptophan derivative, naturally occurring C-glycosyl amino acid found in human ribonuclease. Synlett, 123-125 (1999).
    • (1999) Synlett , vol.123-125
    • Nishikawa, T.1    Ishikawa, M.2    Isobe, M.3
  • 8
    • 0034976370 scopus 로고    scopus 로고
    • Total synthesis of α-C-mannosyltryptophan, a naturally occurring C-glycosyl amino acid
    • Nishikawa, T., Ishikawa, M., Wada, K., and Isobe, M., Total synthesis of α-C-mannosyltryptophan, a naturally occurring C-glycosyl amino acid. Synlett, 945-947 (2001).
    • (2001) Synlett , vol.945-947
    • Nishikawa, T.1    Ishikawa, M.2    Wada, K.3    Isobe, M.4
  • 9
    • 0034577985 scopus 로고    scopus 로고
    • Protein C-mannosylation: Facts and questions
    • Furmanek, A., and Hofsteenge, J., Protein C-mannosylation: facts and questions. Acta Biochimica Polonica, 47, 781-789 (2000).
    • (2000) Acta Biochimica Polonica , vol.47 , pp. 781-789
    • Furmanek, A.1    Hofsteenge, J.2
  • 10
    • 0142099039 scopus 로고    scopus 로고
    • Synthesis of novel α-C-glycosylamino acids and reverse regioselectivity in Larock's heteroannulation for the synthesis of the indole nucleus
    • Nishikawa, T., Wada, K., and Isobe, M., Synthesis of novel α-C-glycosylamino acids and reverse regioselectivity in Larock's heteroannulation for the synthesis of the indole nucleus. Biosci. Biotechnol. Biochem., 66, 2273-2278 (2002).
    • (2002) Biosci. Biotechnol. Biochem , vol.66 , pp. 2273-2278
    • Nishikawa, T.1    Wada, K.2    Isobe, M.3
  • 11
    • 9344261461 scopus 로고    scopus 로고
    • A facile regiocontrol in the palladium-catalyzed annulation of fluorine-containing internal alkynes with variously substituted 2-iodoanilines: A new regioselective synthesis of 2- or 3-fluoroalkylated indole derivatives
    • Konno, T., Chae, J., Ishihara, T., and Yamanaka, H., A facile regiocontrol in the palladium-catalyzed annulation of fluorine-containing internal alkynes with variously substituted 2-iodoanilines: a new regioselective synthesis of 2- or 3-fluoroalkylated indole derivatives. J. Org. Chem., 69, 8258-8265 (2004).
    • (2004) J. Org. Chem , vol.69 , pp. 8258-8265
    • Konno, T.1    Chae, J.2    Ishihara, T.3    Yamanaka, H.4
  • 12
    • 8744296110 scopus 로고    scopus 로고
    • The first regioselective palladium-catalyzed indolization of 2-bromo- or 2-chloroanilines with internal alkynes: A new approach to 2,3-disubstituted indoles
    • Shen, M., Li, G., Lu, B. Z., Hossain, A., Roschangar, F., Farina, V., and Senanayake, C. H., The first regioselective palladium-catalyzed indolization of 2-bromo- or 2-chloroanilines with internal alkynes: a new approach to 2,3-disubstituted indoles. Org. Lett., 6, 4129-4132 (2004).
    • (2004) Org. Lett , vol.6 , pp. 4129-4132
    • Shen, M.1    Li, G.2    Lu, B.Z.3    Hossain, A.4    Roschangar, F.5    Farina, V.6    Senanayake, C.H.7
  • 14
    • 0024584793 scopus 로고
    • 2,2-Difluoro-5-hexyne-1,4- diamine. A potent enzyme-activated inhibitor of ornithine decarboxylase
    • Kendrick, D. A., Danzin, C., and Kolb, M., 2,2-Difluoro-5-hexyne-1,4- diamine. A potent enzyme-activated inhibitor of ornithine decarboxylase. J. Med. Chem., 32, 170-173 (1989).
    • (1989) J. Med. Chem , vol.32 , pp. 170-173
    • Kendrick, D.A.1    Danzin, C.2    Kolb, M.3
  • 15
    • 2542516257 scopus 로고    scopus 로고
    • Design, synthesis, and structure-activity relationships of haloenol lactones: Site-directed and isozyme-selective glutathione S-transferase inhibitors
    • Wu, Z., Minhas, G. S., Wen, D., Jiang, H., Chen, K., Zimniak, P., and Zheng, J., Design, synthesis, and structure-activity relationships of haloenol lactones: site-directed and isozyme-selective glutathione S-transferase inhibitors. J. Med. Chem., 47, 3282-3294 (2004).
    • (2004) J. Med. Chem , vol.47 , pp. 3282-3294
    • Wu, Z.1    Minhas, G.S.2    Wen, D.3    Jiang, H.4    Chen, K.5    Zimniak, P.6    Zheng, J.7
  • 17
  • 18
    • 33645297695 scopus 로고    scopus 로고
    • Synthesis of β-analogues of C-mannosyltryptophan, a novel C-glycosylamino acid found in proteins
    • Nishikawa, T., Koide, Y., Kanakubo, A., Yoshimura, H., and Isobe, M., Synthesis of β-analogues of C-mannosyltryptophan, a novel C-glycosylamino acid found in proteins. Org. Biomol. Chem., 4, 1268-1277 (2006).
    • (2006) Org. Biomol. Chem , vol.4 , pp. 1268-1277
    • Nishikawa, T.1    Koide, Y.2    Kanakubo, A.3    Yoshimura, H.4    Isobe, M.5
  • 19
    • 0032567302 scopus 로고    scopus 로고
    • Novel type of rigid C-linked glycosylacetylene-phenylalanine building blocks for combinatorial synthesis of C-linked glycopeptides
    • Lowary, T., Meldal, M., Helmboldt, A., Vasella, A., and Bock, K., Novel type of rigid C-linked glycosylacetylene-phenylalanine building blocks for combinatorial synthesis of C-linked glycopeptides. J. Org. Chem., 63, 9657-9668 (1998).
    • (1998) J. Org. Chem , vol.63 , pp. 9657-9668
    • Lowary, T.1    Meldal, M.2    Helmboldt, A.3    Vasella, A.4    Bock, K.5
  • 20
    • 0032556811 scopus 로고    scopus 로고
    • Stereocontrolled synthesis and reactivity of sugar acetylenes
    • Isobe, M., Nishizawa, R., Hosokawa, S., and Nishikawa, T., Stereocontrolled synthesis and reactivity of sugar acetylenes. Chem. Commun., 2665-2676 (1998).
    • (1998) Chem. Commun , pp. 2665-2676
    • Isobe, M.1    Nishizawa, R.2    Hosokawa, S.3    Nishikawa, T.4
  • 21
    • 0001777202 scopus 로고    scopus 로고
    • New synthesis with acetylene biscobalthexacarbonyl complex (1)
    • in Japanese
    • Isobe, M., and Kira, K., New synthesis with acetylene biscobalthexacarbonyl complex (1). Yûkigouseikagaku Kyoukaishi (in Japanese), 58, 23-30 (2000).
    • (2000) Yûkigouseikagaku Kyoukaishi , vol.58 , pp. 23-30
    • Isobe, M.1    Kira, K.2
  • 22
    • 0008547529 scopus 로고    scopus 로고
    • New synthesis with acetylene biscobalthexacarbonyl complex (2)
    • in Japanese
    • Isobe, M., and Kira, K., New synthesis with acetylene biscobalthexacarbonyl complex (2). Yûkigouseikagaku Kyoukaishi (in Japanese), 58, 99-107 (2000).
    • (2000) Yûkigouseikagaku Kyoukaishi , vol.58 , pp. 99-107
    • Isobe, M.1    Kira, K.2
  • 23
    • 0344163125 scopus 로고
    • Oxido alcohols and ketoxides
    • Fieser, L. F., and Goto, T., Oxido alcohols and ketoxides. J. Am. Chem. Soc., 82, 1693-1697 (1960).
    • (1960) J. Am. Chem. Soc , vol.82 , pp. 1693-1697
    • Fieser, L.F.1    Goto, T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.