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Volumn 5, Issue 21, 2003, Pages 3883-3885

Stereoselective Construction of cis-2,6-Disubstituted Tetrahydropyrans via the Reductive Etherification of δ-Trialkylsilyloxy Substituted Ketones: Total Synthesis of (-)-Centrolobine

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; ANTIBIOTIC AGENT; CENTROLOBINE; KETONE DERIVATIVE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0242460254     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035438t     Document Type: Article
Times cited : (107)

References (22)
  • 1
    • 0032552046 scopus 로고    scopus 로고
    • and pertinent references therein
    • For a review on recent advances in the stereoselective construction of C-Glycosides, see: Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913 and pertinent references therein.
    • (1998) Tetrahedron , vol.54 , pp. 9913
    • Du, Y.1    Linhardt, R.J.2    Vlahov, I.R.3
  • 3
    • 33845554860 scopus 로고
    • For closely related approaches to the formation of C-glycosides involving nucleophilic addition to oxocarbenium ions, see: (a) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976. (b) Sassaman, M. B.; Prakash, G. K. S.; Olah, G. A. Tetrahedron 1988, 44, 3771. (c) Homma, K.; Mukaiyama, T. Chem. Lett. 1989, 259 and pertinent references therein.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 4976
    • Lewis, M.D.1    Cha, J.K.2    Kishi, Y.3
  • 4
    • 0007214231 scopus 로고
    • For closely related approaches to the formation of C-glycosides involving nucleophilic addition to oxocarbenium ions, see: (a) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976. (b) Sassaman, M. B.; Prakash, G. K. S.; Olah, G. A. Tetrahedron 1988, 44, 3771. (c) Homma, K.; Mukaiyama, T. Chem. Lett. 1989, 259 and pertinent references therein.
    • (1988) Tetrahedron , vol.44 , pp. 3771
    • Sassaman, M.B.1    Prakash, G.K.S.2    Olah, G.A.3
  • 5
    • 33845554860 scopus 로고
    • and pertinent references therein
    • For closely related approaches to the formation of C-glycosides involving nucleophilic addition to oxocarbenium ions, see: (a) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976. (b) Sassaman, M. B.; Prakash, G. K. S.; Olah, G. A. Tetrahedron 1988, 44, 3771. (c) Homma, K.; Mukaiyama, T. Chem. Lett. 1989, 259 and pertinent references therein.
    • (1989) Chem. Lett. , pp. 259
    • Homma, K.1    Mukaiyama, T.2
  • 6
    • 0004285776 scopus 로고    scopus 로고
    • Suzuki, H., Matano, Y., Eds.; Elsevier: New York, Chapter 2
    • Matano, Y.; Ikegami, T. In Organobismuth Chemistry; Suzuki, H., Matano, Y., Eds.; Elsevier: New York, 2001; Chapter 2, pp 21-245.
    • (2001) Organobismuth Chemistry , pp. 21-245
    • Matano, Y.1    Ikegami, T.2
  • 7
  • 11
    • 0037119785 scopus 로고    scopus 로고
    • For an alternative mechanistic proposal that suggests the triethylsilyl bromide formed from triethylsilane and bismuth tribromide behaves as a Lewis acid catalyst, see: Bajwa, J. S.; Jiang, X.; Slade, J.; Prasad, K.; Repic, O.; Blacklock, T. J. Tetrahedron Lett. 2002, 43, 6709.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 6709
    • Bajwa, J.S.1    Jiang, X.2    Slade, J.3    Prasad, K.4    Repic, O.5    Blacklock, T.J.6
  • 12
    • 0242595145 scopus 로고    scopus 로고
    • note
    • The addition of water (100 mol %) afforded the cyclic ether 2 in quantitative yield and with excellent selectivity (entry 4). This further supports the notion that triethylsilyl bromide is not the active catalyst.
  • 14
    • 0242510406 scopus 로고    scopus 로고
    • note
    • Interestingly, the nature of the triorganosilyloxy protecting group is inconsequential in terms of the overall reaction efficiency and selectivity (TES ∼ TBS ∼ TIPS).
  • 16
    • 0034639452 scopus 로고    scopus 로고
    • For a discussion of substituent effects on the stereochemical outcome of additions to tetrahydropyran-derived oxocarbenium ions, see: Romero, J. A. C.; Tabacco, S. A.; Woerpel, K. A. J. Am. Chem. Soc. 2000, 122, 168.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 168
    • Romero, J.A.C.1    Tabacco, S.A.2    Woerpel, K.A.3
  • 22
    • 0038215596 scopus 로고    scopus 로고
    • Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783. For a recent review on olefin cross-metathesis, see: Connon, S. J.; Blechert, S. Angew. Chem. Int. Ed. 2003, 42, 1900.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 1900
    • Connon, S.J.1    Blechert, S.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.