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Volumn , Issue 11, 2003, Pages 1752-1754

Transition metal complexes in organic synthesis, part 69. Total synthesis of the Amaryllidaceae alkaloids anhydrolycorinone and hippadine using iron-and palladium-mediated coupling reactions

Author keywords

Alkaloids; Cyclizations; Dehydrogenations; Iron; Palladium

Indexed keywords

ALIPHATIC AMINE; ALKALOID DERIVATIVE; ANHYDROLYCORINONE; HIPPADINE; IRON COMPLEX; PALLADIUM COMPLEX; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

EID: 0042912835     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41438     Document Type: Article
Times cited : (25)

References (31)
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    • For some recent syntheses, see: (a) Harrowven, D. C.; Lai, D.; Lucas, M. C. Synthesis 1999, 1300. (b) Miki, Y.; Shirokoshi, H.; Matsushita, K. Tetrahedron Lett. 1999, 40, 4347. (c) Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595. (d) Stark, L. M.; Lin, X.-F.; Flippin, L. A. J. Org. Chem. 2000, 65, 3227. (e) Boger, D. L.; Wolkenberg, S. E. J. Org. Chem. 2000, 65, 9120. (f) Wolkenberg, S. E.; Boger, D. L. J. Org. Chem. 2002, 67, 7361; and references cited therein.
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    • For some recent syntheses, see: (a) Harrowven, D. C.; Lai, D.; Lucas, M. C. Synthesis 1999, 1300. (b) Miki, Y.; Shirokoshi, H.; Matsushita, K. Tetrahedron Lett. 1999, 40, 4347. (c) Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595. (d) Stark, L. M.; Lin, X.-F.; Flippin, L. A. J. Org. Chem. 2000, 65, 3227. (e) Boger, D. L.; Wolkenberg, S. E. J. Org. Chem. 2000, 65, 9120. (f) Wolkenberg, S. E.; Boger, D. L. J. Org. Chem. 2002, 67, 7361; and references cited therein.
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    • Miki, Y.1    Shirokoshi, H.2    Matsushita, K.3
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    • 0032900708 scopus 로고    scopus 로고
    • For some recent syntheses, see: (a) Harrowven, D. C.; Lai, D.; Lucas, M. C. Synthesis 1999, 1300. (b) Miki, Y.; Shirokoshi, H.; Matsushita, K. Tetrahedron Lett. 1999, 40, 4347. (c) Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595. (d) Stark, L. M.; Lin, X.-F.; Flippin, L. A. J. Org. Chem. 2000, 65, 3227. (e) Boger, D. L.; Wolkenberg, S. E. J. Org. Chem. 2000, 65, 9120. (f) Wolkenberg, S. E.; Boger, D. L. J. Org. Chem. 2002, 67, 7361; and references cited therein.
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    • 0034685857 scopus 로고    scopus 로고
    • For some recent syntheses, see: (a) Harrowven, D. C.; Lai, D.; Lucas, M. C. Synthesis 1999, 1300. (b) Miki, Y.; Shirokoshi, H.; Matsushita, K. Tetrahedron Lett. 1999, 40, 4347. (c) Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595. (d) Stark, L. M.; Lin, X.-F.; Flippin, L. A. J. Org. Chem. 2000, 65, 3227. (e) Boger, D. L.; Wolkenberg, S. E. J. Org. Chem. 2000, 65, 9120. (f) Wolkenberg, S. E.; Boger, D. L. J. Org. Chem. 2002, 67, 7361; and references cited therein.
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    • For some recent syntheses, see: (a) Harrowven, D. C.; Lai, D.; Lucas, M. C. Synthesis 1999, 1300. (b) Miki, Y.; Shirokoshi, H.; Matsushita, K. Tetrahedron Lett. 1999, 40, 4347. (c) Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595. (d) Stark, L. M.; Lin, X.-F.; Flippin, L. A. J. Org. Chem. 2000, 65, 3227. (e) Boger, D. L.; Wolkenberg, S. E. J. Org. Chem. 2000, 65, 9120. (f) Wolkenberg, S. E.; Boger, D. L. J. Org. Chem. 2002, 67, 7361; and references cited therein.
    • (2000) J. Org. Chem. , vol.65 , pp. 9120
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    • and references cited therein
    • For some recent syntheses, see: (a) Harrowven, D. C.; Lai, D.; Lucas, M. C. Synthesis 1999, 1300. (b) Miki, Y.; Shirokoshi, H.; Matsushita, K. Tetrahedron Lett. 1999, 40, 4347. (c) Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595. (d) Stark, L. M.; Lin, X.-F.; Flippin, L. A. J. Org. Chem. 2000, 65, 3227. (e) Boger, D. L.; Wolkenberg, S. E. J. Org. Chem. 2000, 65, 9120. (f) Wolkenberg, S. E.; Boger, D. L. J. Org. Chem. 2002, 67, 7361; and references cited therein.
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    • Wolkenberg, S.E.1    Boger, D.L.2
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    • note
    • 2), 108.05 (CH), 110.82 (CH), 116.71 (C), 118.38 (CH), 122.51 (C), 122.63 (CH), 123.55 (CH), 124.00 (CH), 128.42 (C), 130.97 (C), 131.66 (C), 148.54 (C), 152.60 (C), 158.19 (C=O).
  • 25
    • 0042038760 scopus 로고    scopus 로고
    • note
    • 2. Removal of the solvent from the combined filtrates and flash chromatography (hexane-EtOAc, 9:1) of the residue on silica gel provided complex 5 as light yellow crystals, yield: 158 mg (86%), mp 122°C.
  • 30
    • 0003441482 scopus 로고
    • Wiley: Chichester
    • For compilations on the Heck reaction, see in: (a) Tsuji, J. Palladium Reagents and Catalysts - Innovations in Organic Synthesis; Wiley: Chichester, 1995. (b) Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry - A Guide for the Synthetic Chemist; Pergamon: Oxford, 2000.
    • (1995) Palladium Reagents and Catalysts - Innovations in Organic Synthesis
    • Tsuji, J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.