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Volumn 8, Issue 17, 2006, Pages 3833-3836

Generation of N-acyliminium ions via intramolecular conjugate addition reactions: A strategy for the total synthesis of nakadomarin A

Author keywords

[No Author keywords available]

Indexed keywords

CARBOLINE DERIVATIVE; IMINE; NAKADOMARIN A;

EID: 33748603473     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061463y     Document Type: Article
Times cited : (39)

References (35)
  • 12
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    • For vicinal difunctionalization of enamides or enecarbamates with carbon electrophiles and carbon nucleophiles via indirect routes, see: (a) Seebach, D.; Stucky, G.; Pfammatter Chem. Ber. 1989, 122, 2377.
    • (1989) Pfammatter Chem. Ber. , vol.122 , pp. 2377
    • Seebach, D.1    Stucky, G.2
  • 17
    • 33847090024 scopus 로고
    • For examples of the enamine variant of this transformation, see: Stevens, R. V. Acc. Chem. Res. 1977, 10, 193.
    • (1977) Acc. Chem. Res. , vol.10 , pp. 193
    • Stevens, R.V.1
  • 18
    • 7744223937 scopus 로고    scopus 로고
    • Suga, S.; Nishida, T.; Yamada, D.; Nagaki, A.; Yoshida, J. J. Am. Chem. Soc. 2004, 126, 14338. This transformation is the converse of the much more well-known tandem vicinal difunctionalization reactions of unsaturated carbonyl systems wherein addition of a nucleophile generates an enolate that is then intercepted by an electrophile.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 14338
    • Suga, S.1    Nishida, T.2    Yamada, D.3    Nagaki, A.4    Yoshida, J.5
  • 20
    • 0037423169 scopus 로고    scopus 로고
    • and references therein
    • The Padwa group has proposed that the N-acyliminium ion 9 arises from a 4π-conrotatory electrocyclization. For additional examples of these Pummerer cyclizations/N-acyliminium ion cyclizations, see: (b) Padwa, A.; Danca, M. D.; Hardcastle, K. I.; McClure, M. S. J. Org. Chem. 2003, 68, 929 and references therein.
    • (2003) J. Org. Chem. , vol.68 , pp. 929
    • Padwa, A.1    Danca, M.D.2    Hardcastle, K.I.3    McClure, M.S.4
  • 21
    • 33745645688 scopus 로고    scopus 로고
    • For a review on Pummerer chemistry, see: (c) Feldman, K. S. Tetrahedron 2006, 62, 5003.
    • (2006) Tetrahedron , vol.62 , pp. 5003
    • Feldman, K.S.1
  • 23
    • 0000872841 scopus 로고    scopus 로고
    • 50 9.9 μg/mL), and antimicrobial activity against a fungus (Trichophyton mentagrophytes, MIC 23 μg/mL) and a Gram-positive bacterium (Corynebacterium xerosis, MIC 11 μg/mL).
    • (1999) Pure Appl. Chem. , vol.71 , pp. 1123
    • Kobayashi, J.1    Tsuda, M.2    Ishibashi, M.3
  • 30
    • 2742547591 scopus 로고    scopus 로고
    • For other examples of intramolecular conjugate addition reactions of α-alkylidene-β-carboxyamides, see: (a) Tietze, L. F.; Schünke, C. Eur. J. Org. Chem. 1998, 2089.
    • (1998) Eur. J. Org. Chem. , pp. 2089
    • Tietze, L.F.1    Schünke, C.2
  • 32
    • 33646155347 scopus 로고    scopus 로고
    • 4, MeOH, rt, 3 h, 81%) of the readily available 3-formylpyrroline; see: Greshock, T. G.; Funk, R. L. J. Am. Chem. Soc. 2006, 128, 4946. For the reductive amination with 3-butynylamine hydrochloride, see ref 8b.
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 4946
    • Greshock, T.G.1    Funk, R.L.2
  • 35
    • 0035826364 scopus 로고    scopus 로고
    • A type 2 intramolecular hetero Diels-Alder reaction pathway is not operative because it can only afford the product with an N-acyliminium ion trans to the furyl substituent upon ring opening of the strained cycloadduct. (Equation Presented) For an attempt to obtain such a cycloadduct, see: Bear, B. R.; Shea, K. J. Org. Lett. 2001, 3, 723.
    • (2001) Org. Lett. , vol.3 , pp. 723
    • Bear, B.R.1    Shea, K.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.