메뉴 건너뛰기




Volumn 42, Issue 33, 2003, Pages 3913-3917

Total synthesis of the ubiquitin-activating enzyme inhibitor (+)-panepophenanthrin

Author keywords

Cycloaddition; Epoxyquinoids; Natural products; Total synthesis

Indexed keywords

BIOSYNTHESIS; DIMERIZATION;

EID: 0041317053     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351862     Document Type: Article
Times cited : (61)

References (47)
  • 1
    • 0031657807 scopus 로고    scopus 로고
    • For recent reviews on the ubiquitin-proteasome pathway, see: a) A. Hershko, A. Ciechanover, Annu. Rev, Biochem. 1998, 67, 425; b) J. Myung, K. B. Kim, C. M. Crews, Med. Res. Rev. 2001, 21,245.
    • (1998) Annu. Rev. Biochem. , vol.67 , pp. 425
    • Hershko, A.1    Ciechanover, A.2
  • 2
    • 0034967925 scopus 로고    scopus 로고
    • For recent reviews on the ubiquitin-proteasome pathway, see: a) A. Hershko, A. Ciechanover, Annu. Rev, Biochem. 1998, 67, 425; b) J. Myung, K. B. Kim, C. M. Crews, Med. Res. Rev. 2001, 21,245.
    • (2001) Med. Res. Rev. , vol.21 , pp. 245
    • Myung, J.1    Kim, K.B.2    Crews, C.M.3
  • 3
    • 0042937859 scopus 로고    scopus 로고
    • For information regarding ubiqutin ligases and relevance to human disease, see: http://www.ligase.com/ligase/si_ligased-iseases.php
  • 6
    • 0031837685 scopus 로고    scopus 로고
    • For a recent review of Diels-Alder-type natural products, see: A. Ichihara, H. Oikawa, Curr Org. Chem. 1998, 2, 365.
    • (1998) Curr Org. Chem. , vol.2 , pp. 365
    • Ichihara, A.1    Oikawa, H.2
  • 13
    • 0037008978 scopus 로고    scopus 로고
    • d) M. Shoji, J. Yamaguchi, H. Kakeya, H. Osada, Y. Hayashi, Angew. Chem. 2002, 114, 3324; Angew. Chem. Int. Ed. 2002, 41, 3192;
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 3192
  • 17
    • 37049097591 scopus 로고
    • For examples of molecules with a hemiacetal bridge formed from a tertiary hydroxy group, see: a) M. Matsuo, S. Matsumoto, Y. Iitaka, A. Hanaki, T. Ozawa, Chem. Commun. 1979, 105; b) D. Martins, E. Osshiro, N. F. Roque, V. Marks, H. E. Gottlies, Phytochemistry 1998, 48, 677.
    • (1979) Chem. Commun. , pp. 105
    • Matsuo, M.1    Matsumoto, S.2    Iitaka, Y.3    Hanaki, A.4    Ozawa, T.5
  • 18
    • 0032102011 scopus 로고    scopus 로고
    • For examples of molecules with a hemiacetal bridge formed from a tertiary hydroxy group, see: a) M. Matsuo, S. Matsumoto, Y. Iitaka, A. Hanaki, T. Ozawa, Chem. Commun. 1979, 105; b) D. Martins, E. Osshiro, N. F. Roque, V. Marks, H. E. Gottlies, Phytochemistry 1998, 48, 677.
    • (1998) Phytochemistry , vol.48 , pp. 677
    • Martins, D.1    Osshiro, E.2    Roque, N.F.3    Marks, V.4    Gottlies, H.E.5
  • 20
    • 0002814116 scopus 로고    scopus 로고
    • The endo [4+2] dimerization appears to be precluded by steric interactions between the epoxide on the dienophile and the diene. For Diels-Alder reactions of 2-vinylcyclohexenones and related dienes, see: a) C. Spino, M. Pesant, Y. Dory, Angew. Chem. 1998, 37, 3454; Angew. Chem. Int. Ed. 1998, 37, 3262; b) J. T. Kuethe, C. A. Brooks, D. L. Comins, Org. Lett. 2003, 5, 321.
    • (1998) Angew. Chem. , vol.37 , pp. 3454
    • Spino, C.1    Pesant, M.2    Dory, Y.3
  • 21
    • 0032542259 scopus 로고    scopus 로고
    • The endo [4+2] dimerization appears to be precluded by steric interactions between the epoxide on the dienophile and the diene. For Diels-Alder reactions of 2-vinylcyclohexenones and related dienes, see: a) C. Spino, M. Pesant, Y. Dory, Angew. Chem. 1998, 37, 3454; Angew. Chem. Int. Ed. 1998, 37, 3262; b) J. T. Kuethe, C. A. Brooks, D. L. Comins, Org. Lett. 2003, 5, 321.
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 3262
  • 22
    • 0038751918 scopus 로고    scopus 로고
    • The endo [4+2] dimerization appears to be precluded by steric interactions between the epoxide on the dienophile and the diene. For Diels-Alder reactions of 2-vinylcyclohexenones and related dienes, see: a) C. Spino, M. Pesant, Y. Dory, Angew. Chem. 1998, 37, 3454; Angew. Chem. Int. Ed. 1998, 37, 3262; b) J. T. Kuethe, C. A. Brooks, D. L. Comins, Org. Lett. 2003, 5, 321.
    • (2003) Org. Lett. , vol.5 , pp. 321
    • Kuethe, J.T.1    Brooks, C.A.2    Comins, D.L.3
  • 26
    • 0035861069 scopus 로고    scopus 로고
    • a) C. Li, E. Pace, M. Liang, E. Lobkovsky, T. D. Gilmore, J. A. Porco, Jr.,J. Am. Chem. Soc. 2001, 123, 11308; For tartrate-mediated epoxidation of acyclic enones, see: b) C. L. Elston, R. F. W. Jackson, S. J. F. MacDonald, P. J. Murray, Angew. Chem. 1997, 36, 379; Angew. Chem. Int. Ed. Engl. 1997, 36, 410; c) O. Jacques, S. J. Richards, R. F. W. Jackson, Chem. Commun. 2001, 2712.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 11308
    • Li, C.1    Pace, E.2    Liang, M.3    Lobkovsky, E.4    Gilmore, T.D.5    Porco J.A., Jr.6
  • 27
    • 0041936164 scopus 로고    scopus 로고
    • a) C. Li, E. Pace, M. Liang, E. Lobkovsky, T. D. Gilmore, J. A. Porco, Jr.,J. Am. Chem. Soc. 2001, 123, 11308; For tartrate-mediated epoxidation of acyclic enones, see: b) C. L. Elston, R. F. W. Jackson, S. J. F. MacDonald, P. J. Murray, Angew. Chem. 1997, 36, 379; Angew. Chem. Int. Ed. Engl. 1997, 36, 410; c) O. Jacques, S. J. Richards, R. F. W. Jackson, Chem. Commun. 2001, 2712.
    • (1997) Angew. Chem. , vol.36 , pp. 379
    • Elston, C.L.1    Jackson, R.F.W.2    MacDonald, S.J.F.3    Murray, P.J.4
  • 28
    • 0030895780 scopus 로고    scopus 로고
    • a) C. Li, E. Pace, M. Liang, E. Lobkovsky, T. D. Gilmore, J. A. Porco, Jr.,J. Am. Chem. Soc. 2001, 123, 11308; For tartrate-mediated epoxidation of acyclic enones, see: b) C. L. Elston, R. F. W. Jackson, S. J. F. MacDonald, P. J. Murray, Angew. Chem. 1997, 36, 379; Angew. Chem. Int. Ed. Engl. 1997, 36, 410; c) O. Jacques, S. J. Richards, R. F. W. Jackson, Chem. Commun. 2001, 2712.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 410
  • 29
    • 0035930788 scopus 로고    scopus 로고
    • a) C. Li, E. Pace, M. Liang, E. Lobkovsky, T. D. Gilmore, J. A. Porco, Jr.,J. Am. Chem. Soc. 2001, 123, 11308; For tartrate-mediated epoxidation of acyclic enones, see: b) C. L. Elston, R. F. W. Jackson, S. J. F. MacDonald, P. J. Murray, Angew. Chem. 1997, 36, 379; Angew. Chem. Int. Ed. Engl. 1997, 36, 410; c) O. Jacques, S. J. Richards, R. F. W. Jackson, Chem. Commun. 2001, 2712.
    • (2001) Chem. Commun. , pp. 2712
    • Jacques, O.1    Richards, S.J.2    Jackson, R.F.W.3
  • 38
    • 0000552007 scopus 로고
    • For ionic Diels-Alder reactions involving hydroxy dienes and cyclic enones, see: a) P. G. Gassman, D. A. Singleton, J. Am. Chem. Soc. 1984, 106, 6085; b) R. K. Haynes, G. R. King, S. C. Vonwiller, J. Org. Chem. 1994, 59, 4743.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 6085
    • Gassman, P.G.1    Singleton, D.A.2
  • 39
    • 0028037751 scopus 로고
    • For ionic Diels-Alder reactions involving hydroxy dienes and cyclic enones, see: a) P. G. Gassman, D. A. Singleton, J. Am. Chem. Soc. 1984, 106, 6085; b) R. K. Haynes, G. R. King, S. C. Vonwiller, J. Org. Chem. 1994, 59, 4743.
    • (1994) J. Org. Chem. , vol.59 , pp. 4743
    • Haynes, R.K.1    King, G.R.2    Vonwiller, S.C.3
  • 44
    • 0013500960 scopus 로고    scopus 로고
    • Analysis by chiral HPLC verified that the crystal was racemic, while the mother liquor was optically pure (see Supporting Information). For an example of a "racemic crystal" formed by crystallization of an optically enriched compound, see: A. Mishnev, I. Iovel, J. Popelis, I. Vosekalna, E. Lukevics, J. Organomet. Chem. 2000, 608, 1.
    • (2000) J. Organomet. Chem. , vol.608 , pp. 1
    • Mishnev, A.1    Iovel, I.2    Popelis, J.3    Vosekalna, I.4    Lukevics, E.5
  • 45
    • 0041936169 scopus 로고    scopus 로고
    • note
    • All calculations were performed with Spartan'02, Wavefunction Inc., Irvine, CA, 2002; see Supporting Information.
  • 46
    • 0042937856 scopus 로고    scopus 로고
    • CCDC-206033 (8) and -206034 (25) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.