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Volumn 350, Issue 14-15, 2008, Pages 2219-2225

Exploiting non-covalent interactions in synthesis: Macrocyclization employing amide-based auxiliaries

Author keywords

Cyclophanes; Macrocyclization; Natural product synthesis; Olefin metathesis; Quadrupolar interactions

Indexed keywords


EID: 55049128543     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800365     Document Type: Article
Times cited : (9)

References (63)
  • 1
    • 19844372066 scopus 로고    scopus 로고
    • For reviews on macrocyclization using metathesis in synthesis, see: a
    • For reviews on macrocyclization using metathesis in synthesis, see: a) J. Blankenstein, J. Zhu, Eur. J. Org. Chem. 2005, 10, 1949-1964;
    • (2005) Eur. J. Org. Chem , vol.10 , pp. 1949-1964
    • Blankenstein, J.1    Zhu, J.2
  • 3
    • 0037122039 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2002, 41, 4632-4653;
    • (2002) Angew. Chem. Int. Ed , vol.41 , pp. 4632-4653
  • 4
    • 0000314051 scopus 로고
    • c) P. Wipf, Chem. Rev. 1995, 95, 2115-2134;
    • (1995) Chem. Rev , vol.95 , pp. 2115-2134
    • Wipf, P.1
  • 5
    • 25444439166 scopus 로고    scopus 로고
    • for a recent example in natural product synthesis, see: d
    • for a recent example in natural product synthesis, see: d) W. H. Kim, J. H. Jung, L. T. Sung, S. M. Lim, E. Lee, Org. Lett. 2005, 7, 1085-1087;
    • (2005) Org. Lett , vol.7 , pp. 1085-1087
    • Kim, W.H.1    Jung, J.H.2    Sung, L.T.3    Lim, S.M.4    Lee, E.5
  • 6
    • 33846815244 scopus 로고    scopus 로고
    • for a discussion on the mechanism of macrocyclization via olefin metathesis, see: e J. C. Conrad, M. D. Eelman, J. A. Duarte Silva, S. Monfette, H. H. Parnas, J. L. Snelgrove, D. E. Fogg, J. Am. Chem. Soc. 2007, 129, 1024-1025;
    • for a discussion on the mechanism of macrocyclization via olefin metathesis, see: e) J. C. Conrad, M. D. Eelman, J. A. Duarte Silva, S. Monfette, H. H. Parnas, J. L. Snelgrove, D. E. Fogg, J. Am. Chem. Soc. 2007, 129, 1024-1025;
  • 11
    • 39549084947 scopus 로고    scopus 로고
    • for recent efforts in catalyst development for macrocyclization see: j
    • for recent efforts in catalyst development for macrocyclization see: j) G. C. Vougioukalakis, R. H. Grubbs, J. Am. Chem. Soc. 2008, 130, 2234-2245;
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 2234-2245
    • Vougioukalakis, G.C.1    Grubbs, R.H.2
  • 12
    • 20444474543 scopus 로고    scopus 로고
    • for examples of macrocyclic ring closing metathesis used in rotaxane synthesis, see: k
    • for examples of macrocyclic ring closing metathesis used in rotaxane synthesis, see: k) E. N. Guidry, S. J. Cantrill, J. F. Stoddart, R. H. Grubbs, Org. Lett. 2005, 7, 2129-2132;
    • (2005) Org. Lett , vol.7 , pp. 2129-2132
    • Guidry, E.N.1    Cantrill, S.J.2    Stoddart, J.F.3    Grubbs, R.H.4
  • 16
    • 4143108202 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 3601-3605;
    • (2004) Angew. Chem. Int. Ed , vol.43 , pp. 3601-3605
  • 23
    • 32044451346 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 968-973;
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 968-973
  • 32
    • 53849128348 scopus 로고    scopus 로고
    • for a discussion on the theory of aromatic-aromatic interactions see: e
    • for a discussion on the theory of aromatic-aromatic interactions see: e) S. Grimme, Angew. Chem. 2008, 120, 3478-3483;
    • (2008) Angew. Chem , vol.120 , pp. 3478-3483
    • Grimme, S.1
  • 33
    • 44949146389 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 3430-3434.
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 3430-3434
  • 35
    • 4544376455 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 3061-3063;
    • (2004) Angew. Chem. Int. Ed , vol.43 , pp. 3061-3063
  • 47
    • 55049141899 scopus 로고    scopus 로고
    • We also attempted to prepare tertiary amide-based auxiliaries for macrocyclization. However, the synthesis of the corresponding amides from N-ethyl-2,3,4,5,6-pentafluorobenzylamine was problematic. Typical peptide couplings (EDC, DCC, HOBt) as well as various reactions involving acyl chlorides failed to afford the desired tertiary amides.
    • We also attempted to prepare tertiary amide-based auxiliaries for macrocyclization. However, the synthesis of the corresponding amides from N-ethyl-2,3,4,5,6-pentafluorobenzylamine was problematic. Typical peptide couplings (EDC, DCC, HOBt) as well as various reactions involving acyl chlorides failed to afford the desired tertiary amides.
  • 48
    • 55049084774 scopus 로고    scopus 로고
    • 3,5-Bis(trifluoromethyl)benzylamine, 80%, Aldrich #26330-1 g, $25.60 US.
    • 3,5-Bis(trifluoromethyl)benzylamine, 80%, Aldrich #26330-1 g, $25.60 US.
  • 51
    • 55049104637 scopus 로고    scopus 로고
    • [5]
    • [5]
  • 53
  • 54
    • 16844366046 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 1912-1915.
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 1912-1915
  • 55
    • 0000652020 scopus 로고    scopus 로고
    • For the isolation of longithorone Csee : a X. Fu, M. B. Hossain, F. J. Schmitz, D. van der Helm, J. Org. Chem. 1997, 62, 3810-3819;
    • For the isolation of longithorone Csee : a) X. Fu, M. B. Hossain, F. J. Schmitz, D. van der Helm, J. Org. Chem. 1997, 62, 3810-3819;
  • 56
    • 0032828449 scopus 로고    scopus 로고
    • for the isolation of other family members, see: b
    • for the isolation of other family members, see: b) X. Fu, M. L. Ferreira, F. J. Schmitz, J. Nat. Prod. 1999, 62, 1306-1310;
    • (1999) J. Nat. Prod , vol.62 , pp. 1306-1310
    • Fu, X.1    Ferreira, M.L.2    Schmitz, F.J.3
  • 59
    • 55049099054 scopus 로고    scopus 로고
    • Although the model systems in our molecular modelling study contain two olefinic sidechains, we believe it is reasonable to assume that similar energetic values would be obtained for en-yne substrates. This based upon the fact that the substitution of an alkyne for a alkene is a minor structural change unlikely to alter the solution state conformations in a significant manner
    • Although the model systems in our molecular modelling study contain two olefinic sidechains, we believe it is reasonable to assume that similar energetic values would be obtained for en-yne substrates. This based upon the fact that the substitution of an alkyne for a alkene is a minor structural change unlikely to alter the solution state conformations in a significant manner.
  • 60
    • 55049140021 scopus 로고    scopus 로고
    • The [12]paracyclophane isolated is the endo-product resulting from en-yne metathesis. The corresponding exo-product is never observed, as it results in the formation of a [11]paracyclophane that is too rigid to form via olefin metathesis.
    • The [12]paracyclophane isolated is the endo-product resulting from en-yne metathesis. The corresponding exo-product is never observed, as it results in the formation of a [11]paracyclophane that is too rigid to form via olefin metathesis.
  • 63
    • 33748232054 scopus 로고
    • Angew. Chem. Int. Ed. 1992, 31, 1655-1657.
    • (1992) Angew. Chem. Int. Ed , vol.31 , pp. 1655-1657


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.