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Volumn 64, Issue 3, 1999, Pages 736-746

Studies of acyl nitrene insertions. A stereocontrolled route toward lankacidin antibiotics

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; FURAN DERIVATIVE; LANKACIDIN; UNCLASSIFIED DRUG;

EID: 0033525175     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981310r     Document Type: Article
Times cited : (25)

References (51)
  • 9
    • 0009528963 scopus 로고
    • For examples of intramolecular azidoformate C-H insertion reactions, see: (a) Berner, H.; Vyplel, H.; Schulz, G.; Stuchlik, P. Tetrahedron 1984, 40, 919. (b) Yuan, P.; Plourde, R.; Shoemaker, M. R.; Moore, C. L.; Hansen, D. E. J. Org. Chem. 1995, 60, 5360. (c) Banks, M. R.; Blake, A. J.; Cadogan, J. I. G.; Dawson, I. M.; Gosney, I.; Grant, K. J.; Gaur, S.; Hodgson, P. K. G.; Knight, K. S.; Smith, G. W.; Stevenson, D. E. Tetrahedron 1992, 48, 7979. For examples of intramolecular C=C insertion reactions of azidoformate-derived acyl nitrenes, see: (d) Rhouati, S.; Bernou, A. J. Chem. Soc., Chem. Commun. 1989, 730. (e) Bergmeier, S. C.; Stanchina, D. M. Tetrahedron Lett. 1995, 36, 4533. (f) Bergmeier, S. C.; Stanchina, D. M. J. Org. Chem. 1997, 62, 4449.
    • (1984) Tetrahedron , vol.40 , pp. 919
    • Berner, H.1    Vyplel, H.2    Schulz, G.3    Stuchlik, P.4
  • 10
    • 0029157125 scopus 로고
    • For examples of intramolecular azidoformate C-H insertion reactions, see: (a) Berner, H.; Vyplel, H.; Schulz, G.; Stuchlik, P. Tetrahedron 1984, 40, 919. (b) Yuan, P.; Plourde, R.; Shoemaker, M. R.; Moore, C. L.; Hansen, D. E. J. Org. Chem. 1995, 60, 5360. (c) Banks, M. R.; Blake, A. J.; Cadogan, J. I. G.; Dawson, I. M.; Gosney, I.; Grant, K. J.; Gaur, S.; Hodgson, P. K. G.; Knight, K. S.; Smith, G. W.; Stevenson, D. E. Tetrahedron 1992, 48, 7979. For examples of intramolecular C=C insertion reactions of azidoformate-derived acyl nitrenes, see: (d) Rhouati, S.; Bernou, A. J. Chem. Soc., Chem. Commun. 1989, 730. (e) Bergmeier, S. C.; Stanchina, D. M. Tetrahedron Lett. 1995, 36, 4533. (f) Bergmeier, S. C.; Stanchina, D. M. J. Org. Chem. 1997, 62, 4449.
    • (1995) J. Org. Chem. , vol.60 , pp. 5360
    • Yuan, P.1    Plourde, R.2    Shoemaker, M.R.3    Moore, C.L.4    Hansen, D.E.5
  • 11
    • 0026697882 scopus 로고
    • For examples of intramolecular azidoformate C-H insertion reactions, see: (a) Berner, H.; Vyplel, H.; Schulz, G.; Stuchlik, P. Tetrahedron 1984, 40, 919. (b) Yuan, P.; Plourde, R.; Shoemaker, M. R.; Moore, C. L.; Hansen, D. E. J. Org. Chem. 1995, 60, 5360. (c) Banks, M. R.; Blake, A. J.; Cadogan, J. I. G.; Dawson, I. M.; Gosney, I.; Grant, K. J.; Gaur, S.; Hodgson, P. K. G.; Knight, K. S.; Smith, G. W.; Stevenson, D. E. Tetrahedron 1992, 48, 7979. For examples of intramolecular C=C insertion reactions of azidoformate-derived acyl nitrenes, see: (d) Rhouati, S.; Bernou, A. J. Chem. Soc., Chem. Commun. 1989, 730. (e) Bergmeier, S. C.; Stanchina, D. M. Tetrahedron Lett. 1995, 36, 4533. (f) Bergmeier, S. C.; Stanchina, D. M. J. Org. Chem. 1997, 62, 4449.
    • (1992) Tetrahedron , vol.48 , pp. 7979
    • Banks, M.R.1    Blake, A.J.2    Cadogan, J.I.G.3    Dawson, I.M.4    Gosney, I.5    Grant, K.J.6    Gaur, S.7    Hodgson, P.K.G.8    Knight, K.S.9    Smith, G.W.10    Stevenson, D.E.11
  • 12
    • 37049070727 scopus 로고
    • For examples of intramolecular azidoformate C-H insertion reactions, see: (a) Berner, H.; Vyplel, H.; Schulz, G.; Stuchlik, P. Tetrahedron 1984, 40, 919. (b) Yuan, P.; Plourde, R.; Shoemaker, M. R.; Moore, C. L.; Hansen, D. E. J. Org. Chem. 1995, 60, 5360. (c) Banks, M. R.; Blake, A. J.; Cadogan, J. I. G.; Dawson, I. M.; Gosney, I.; Grant, K. J.; Gaur, S.; Hodgson, P. K. G.; Knight, K. S.; Smith, G. W.; Stevenson, D. E. Tetrahedron 1992, 48, 7979. For examples of intramolecular C=C insertion reactions of azidoformate-derived acyl nitrenes, see: (d) Rhouati, S.; Bernou, A. J. Chem. Soc., Chem. Commun. 1989, 730. (e) Bergmeier, S. C.; Stanchina, D. M. Tetrahedron Lett. 1995, 36, 4533. (f) Bergmeier, S. C.; Stanchina, D. M. J. Org. Chem. 1997, 62, 4449.
    • (1989) J. Chem. Soc., Chem. Commun. , pp. 730
    • Rhouati, S.1    Bernou, A.2
  • 13
    • 0029002279 scopus 로고
    • For examples of intramolecular azidoformate C-H insertion reactions, see: (a) Berner, H.; Vyplel, H.; Schulz, G.; Stuchlik, P. Tetrahedron 1984, 40, 919. (b) Yuan, P.; Plourde, R.; Shoemaker, M. R.; Moore, C. L.; Hansen, D. E. J. Org. Chem. 1995, 60, 5360. (c) Banks, M. R.; Blake, A. J.; Cadogan, J. I. G.; Dawson, I. M.; Gosney, I.; Grant, K. J.; Gaur, S.; Hodgson, P. K. G.; Knight, K. S.; Smith, G. W.; Stevenson, D. E. Tetrahedron 1992, 48, 7979. For examples of intramolecular C=C insertion reactions of azidoformate-derived acyl nitrenes, see: (d) Rhouati, S.; Bernou, A. J. Chem. Soc., Chem. Commun. 1989, 730. (e) Bergmeier, S. C.; Stanchina, D. M. Tetrahedron Lett. 1995, 36, 4533. (f) Bergmeier, S. C.; Stanchina, D. M. J. Org. Chem. 1997, 62, 4449.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 4533
    • Bergmeier, S.C.1    Stanchina, D.M.2
  • 14
    • 0000890629 scopus 로고    scopus 로고
    • For examples of intramolecular azidoformate C-H insertion reactions, see: (a) Berner, H.; Vyplel, H.; Schulz, G.; Stuchlik, P. Tetrahedron 1984, 40, 919. (b) Yuan, P.; Plourde, R.; Shoemaker, M. R.; Moore, C. L.; Hansen, D. E. J. Org. Chem. 1995, 60, 5360. (c) Banks, M. R.; Blake, A. J.; Cadogan, J. I. G.; Dawson, I. M.; Gosney, I.; Grant, K. J.; Gaur, S.; Hodgson, P. K. G.; Knight, K. S.; Smith, G. W.; Stevenson, D. E. Tetrahedron 1992, 48, 7979. For examples of intramolecular C=C insertion reactions of azidoformate-derived acyl nitrenes, see: (d) Rhouati, S.; Bernou, A. J. Chem. Soc., Chem. Commun. 1989, 730. (e) Bergmeier, S. C.; Stanchina, D. M. Tetrahedron Lett. 1995, 36, 4533. (f) Bergmeier, S. C.; Stanchina, D. M. J. Org. Chem. 1997, 62, 4449.
    • (1997) J. Org. Chem. , vol.62 , pp. 4449
    • Bergmeier, S.C.1    Stanchina, D.M.2
  • 32
    • 0003689435 scopus 로고
    • Freeman, J. P., Ed.; Wiley: New York, Collect. and references therein
    • (a) Gage, J. R.; Evans, D. A. In Organic Syntheses; Freeman, J. P., Ed.; Wiley: New York, 1993; Collect. Vol. VIII, p 528, and references therein.
    • (1993) Organic Syntheses , vol.8 , pp. 528
    • Gage, J.R.1    Evans, D.A.2
  • 33
    • 0000830549 scopus 로고
    • Freeman, J. P., Ed.; Wiley: New York, Collect. and references therein
    • (b) Gage, J. R.; Evans, D. A. In Organic Syntheses; Freeman, J. P., Ed.; Wiley: New York, 1993; Collect. Vol. VIII, p 339, and references therein.
    • (1993) Organic Syntheses , vol.8 , pp. 339
    • Gage, J.R.1    Evans, D.A.2
  • 35
    • 0001414628 scopus 로고
    • Wiley: New York, Collect. and references therein
    • (b) Seebach, D.; Aebi, J.; Wasmuth, D. In Organic Syntheses; Wiley: New York, 1990; Collect. Vol. VII, p 153, and references therein.
    • (1990) Organic Syntheses , vol.7 , pp. 153
    • Seebach, D.1    Aebi, J.2    Wasmuth, D.3
  • 39
    • 0345400925 scopus 로고
    • Ph.D. Thesis, Indiana University
    • Rieger, D. L. Ph.D. Thesis, Indiana University, 1989; pp 95-99.
    • (1989) , pp. 95-99
    • Rieger, D.L.1
  • 40
    • 33947299760 scopus 로고
    • For examples of N-acylaziridine to oxazoline rearrangements, see: (a) Nishiguchi, T.; Tochio, H.; Nabeya, A.; Iwakura, Y. J. Am. Chem. Soc. 1969, 91, 5835. (b) Allemann, S.; Vogel, P. Synthesis 1991, 923. (c) Ferraris, D.; Drury, W. J., III.; Cox, C.; Lectka, T. J. Org. Chem. 1998, 63, 4568.
    • (1969) J. Am. Chem. Soc. , vol.91 , pp. 5835
    • Nishiguchi, T.1    Tochio, H.2    Nabeya, A.3    Iwakura, Y.4
  • 41
    • 0025948459 scopus 로고
    • For examples of N-acylaziridine to oxazoline rearrangements, see: (a) Nishiguchi, T.; Tochio, H.; Nabeya, A.; Iwakura, Y. J. Am. Chem. Soc. 1969, 91, 5835. (b) Allemann, S.; Vogel, P. Synthesis 1991, 923. (c) Ferraris, D.; Drury, W. J., III.; Cox, C.; Lectka, T. J. Org. Chem. 1998, 63, 4568.
    • (1991) Synthesis , pp. 923
    • Allemann, S.1    Vogel, P.2
  • 42
    • 0001009177 scopus 로고    scopus 로고
    • For examples of N-acylaziridine to oxazoline rearrangements, see: (a) Nishiguchi, T.; Tochio, H.; Nabeya, A.; Iwakura, Y. J. Am. Chem. Soc. 1969, 91, 5835. (b) Allemann, S.; Vogel, P. Synthesis 1991, 923. (c) Ferraris, D.; Drury, W. J., III.; Cox, C.; Lectka, T. J. Org. Chem. 1998, 63, 4568.
    • (1998) J. Org. Chem. , vol.63 , pp. 4568
    • Ferraris, D.1    Drury W.J. III2    Cox, C.3    Lectka, T.4
  • 43
    • 0344969517 scopus 로고    scopus 로고
    • note
    • Data resulting from the X-ray diffraction studies for crystals of compounds 5, 21, and 34b have been deposited with the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K. We acknowledge the collaborative efforts of J. C. Huffman, K. F. Streib, and W. C. Streib of the Indiana University Molecular Structure Center (Reports 93254, 93082, and 91057).
  • 44
    • 0000478917 scopus 로고
    • Optically active dihydrofuran 30 was produced via reduction of (4S,5R)-4,5-dihydro-5-(tert-butyldiphenylsilyloxymethyl)-4-methyl-2(3H)- furanone, which was prepared from D-glutamic acid following the literature for the enantiomeric butenolide. Hanessian, S.; Murray, P. J. J. Org. Chem. 1987, 52, 1170.
    • (1987) J. Org. Chem. , vol.52 , pp. 1170
    • Hanessian, S.1    Murray, P.J.2
  • 48
    • 0345400924 scopus 로고    scopus 로고
    • note
    • Benzyl azidoformate was prepared following adaptation of the published procedure for ethyl azidoformate (ref 20).


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