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Volumn 8, Issue 23, 2006, Pages 5271-5273

Tandem semipinacol/Schmidt reaction leading to a versatile and efficient approach to azaquaternary alkaloid skeletons

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EID: 33845240745     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062116r     Document Type: Article
Times cited : (37)

References (37)
  • 4
    • 0141520491 scopus 로고    scopus 로고
    • and references therein
    • (c) Li, W.-D. Z.; Wang, Y.-Q. Org. Lett. 2003, 5, 2931-2934 and references therein.
    • (2003) Org. Lett. , vol.5 , pp. 2931-2934
    • Li, W.-D.Z.1    Wang, Y.-Q.2
  • 5
    • 33745725808 scopus 로고    scopus 로고
    • and other strategies cited therein
    • Recently, we have developed an efficient strategy for erythrinan and homoerythrinan alkaloids. See: Gao, S.; Tu, Y. Q.; Hu, X.; Wang, S.; Hua, R.; Jiang, Y.; Zhao, Y.; Fan, X.; Zhang, S. Org. Lett. 2006, 8, 2373-2376 and other strategies cited therein.
    • (2006) Org. Lett. , vol.8 , pp. 2373-2376
    • Gao, S.1    Tu, Y.Q.2    Hu, X.3    Wang, S.4    Hua, R.5    Jiang, Y.6    Zhao, Y.7    Fan, X.8    Zhang, S.9
  • 8
    • 0036263802 scopus 로고    scopus 로고
    • and references therein
    • Angew. Chem., Int. Ed. 2002, 41, 1783-1785 and references therein.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 1783-1785
  • 9
    • 0037241493 scopus 로고    scopus 로고
    • For reviews on total synthesis of the cylindricine/fasicularin/ lepadiformine family of tricyclic marine alkaloids, see: (a) Weinreb, S. M. Acc. Chem. Res. 2003, 36, 59-65.
    • (2003) Acc. Chem. Res. , vol.36 , pp. 59-65
    • Weinreb, S.M.1
  • 10
    • 33745698645 scopus 로고    scopus 로고
    • (b) Weinreb, S. M. Chem. Rev. 2006, 106, 2531-2549.
    • (2006) Chem. Rev. , vol.106 , pp. 2531-2549
    • Weinreb, S.M.1
  • 13
  • 15
  • 24
    • 84886199418 scopus 로고
    • For studies of the intramolecular Schmidt reaction, please see: (a) Aubé, J.; Milligan, G. L. J. Am. Chem. Soc. 1991, 113, 8965-8966.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 8965-8966
    • Aubé, J.1    Milligan, G.L.2
  • 26
    • 2242455044 scopus 로고    scopus 로고
    • For a domino reaction involving an intramolecular Schmidt reaction, see: (a) Golden, J. E.; Aubé, J. Angew. Chem., Int. Ed. 2002, 41, 4316-4318.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 4316-4318
    • Golden, J.E.1    Aubé, J.2
  • 29
    • 0141741413 scopus 로고    scopus 로고
    • For additional examples involving rearrangement of epoxy-azides, see: (a) Reddy, P. G.; Varghese, B.; Baskaran, S. Org. Lett. 2003, 5, 583-585.
    • (2003) Org. Lett. , vol.5 , pp. 583-585
    • Reddy, P.G.1    Varghese, B.2    Baskaran, S.3
  • 32
    • 33845273241 scopus 로고    scopus 로고
    • note
    • CAUTION! Alkyl azides are potential explosion hazards in substrate synthesis. See the Supporting Information.
  • 33
    • 33845255424 scopus 로고    scopus 로고
    • note
    • The mixtures of 2i and 2j were formed from the corresponding mixed substrates 1i and 1j, respectively.
  • 35
    • 0043127350 scopus 로고    scopus 로고
    • For tandem asymmetric allylation/diastereoselective epoxidation of cyclic enones, see: (a) Jeon, S.-J.; Walsh, P. J. J Am. Chem. Soc. 2003, 125, 9544-9545.
    • (2003) J Am. Chem. Soc. , vol.125 , pp. 9544-9545
    • Jeon, S.-J.1    Walsh, P.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.