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Volumn 111, Issue 8, 1989, Pages 2967-2980

The Total Synthesis of Avermectin A1a

Author keywords

[No Author keywords available]

Indexed keywords

AVERMECTIN A1 A; DRUG ANALYSIS; DRUG DEVELOPMENT; DRUG STRUCTURE; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE;

EID: 0024589836     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00190a034     Document Type: Article
Times cited : (157)

References (50)
  • 6
    • 85022478282 scopus 로고    scopus 로고
    • Janes, N. F., Ed.; Royal Society of Chemistry: London and references therein
    • Fisher, M. H. Recent Advances in the Chemistry of Insect Control; Janes, N. F., Ed.; Royal Society of Chemistry: London, 1985; p 53 and references therein
    • Recent Advances in the Chemistry of Insect Control , pp. 1985
    • Fisher, M.H.1
  • 7
    • 0020466216 scopus 로고
    • Chabala, J. C.; Mrozik, H.; Tolman, R. L.; Eskola, P.; Lusi, A.; Peterson, L. H.; Woods, M. F.; Fisher, M. H.; Cambell, W. C.; Egerton, J. R., Ostlind, D. A. J. Med. Chem. 1980, 23, 1134
    • Mrozik, H.; Eskola, P.; Fisher, M. H., Egerton, J. R.; Cifelli, S.; Ostlind, D. A. J. Med. Chem. 1982, 25, 658. (b) Chabala, J. C.; Mrozik, H.; Tolman, R. L.; Eskola, P.; Lusi, A.; Peterson, L. H.; Woods, M. F.; Fisher, M. H.; Cambell, W. C.; Egerton, J. R., Ostlind, D. A. J. Med. Chem. 1980, 23, 1134
    • (1982) J. Med. Chem , vol.25 , pp. 658
    • Mrozik, H.1    Eskola, P.2    Fisher, M.H.3    Egerton, J.R.4    Cifelli, S.5    Ostlind, D.A.6
  • 8
    • 0022697736 scopus 로고
    • For a recent review of related milbemycin syntheses, see
    • For a recent review of related milbemycin syntheses, see: Davies, H. G.; Green, R. H. Nat. Prod. Rep. 1986, 87
    • (1986) Nat. Prod. Rep , pp. 87
    • Davies, H.G.1    Green, R.H.2
  • 12
    • 84944225033 scopus 로고
    • For previous syntheses of milbemycin and avermectin spiroketals, cf. interalia Baker, R.; Boyes, R. H. O.; Broom, D. M. P.; Devlin, J. A.; Swain, C. J. J. Chem. Soc., Chem. Commun. 1983, 829. (c) Baker, R.; Swain, C. J.; Head, J. C. J. Chem. Soc., Chem. Commun. 1985, 309. (d) Hanessian, S.; Ugolini, A.; Therien, M. J. Org. Chem. 1983, 48, 4427. (e) Culshaw, D.; Grice, P.; Ley, S. V.; Strange, G. A. Tetrahedron Lett. 1985, 26, 5837. (f) Ardisson, J.; Ferezou, J. P.; Julia, M.; Lenglet, L.; Pancrazi, A. Tetrahedron Lett. 1987, 28, 1997. (g) Attwood, S. V.; Barrett, A. G. M.; Carr, R. A. E.; Richardson, G. J. Chem. Soc., Chem. Commun. 1986, 479
    • For previous syntheses of milbemycin and avermectin spiroketals, cf. interalia: (a) Street, D. A.; Kocienski, P.; Campbell, S. F. J. Chem. Soc., Chem. Commun. 1985, 1326. (b) Baker, R.; Boyes, R. H. O.; Broom, D. M. P.; Devlin, J. A.; Swain, C. J. J. Chem. Soc., Chem. Commun. 1983, 829. (c) Baker, R.; Swain, C. J.; Head, J. C. J. Chem. Soc., Chem. Commun. 1985, 309. (d) Hanessian, S.; Ugolini, A.; Therien, M. J. Org. Chem. 1983, 48, 4427. (e) Culshaw, D.; Grice, P.; Ley, S. V.; Strange, G. A. Tetrahedron Lett. 1985, 26, 5837. (f) Ardisson, J.; Ferezou, J. P.; Julia, M.; Lenglet, L.; Pancrazi, A. Tetrahedron Lett. 1987, 28, 1997. (g) Attwood, S. V.; Barrett, A. G. M.; Carr, R. A. E.; Richardson, G. J. Chem. Soc., Chem. Commun. 1986, 479
    • (1985) J. Chem. Soc., Chem. Commun , pp. 1326
    • Street, D.A.1    Kocienski, P.2    Campbell, S.F.3
  • 13
    • 33645171082 scopus 로고
    • For synthetic studies related to the oxahydrindrene portion of the avermectins, see Kozikowski, A. P.; MaloneyHuss, K. E. Tetrahedron Lett. 1985, 26, 5759. (c) Prashad, M.; Fraser-Reid, B. J. Org. Chem. 1985, 50, 1564. (d) Crimmins, M. T.; Lever, J. G. Tetrahedron Lett. 1986, 27, 291. (e) Ireland, R. E.; Obrecht, D. M. Helv. Chim. Acta 1986, 69, 1273. (f) Hanessian, S.; Beaulieu, P.; Dube, D. Tetrahedron Lett. 1986, 27, 5071. (g) Barrett, A. G. M.; Capps, N. K. Tetrahedron Lett. 1986, 27, 5571. (h) Jung, M. E.; Street, L. H.; Usui, Y. J. Am. Chem. Soc. 1986, 108, 6810. (i) Ardisson, J.; Ferezou, J. P.; Julia, M.; Pancrazi, A. Tetrahedron Lett. 1987, 28, 2001
    • For synthetic studies related to the oxahydrindrene portion of the avermectins, see: (a) Jung, M. E.; Street, L. J. J. Am. Chem. Soc. 1984, 106, 8327. (b) Kozikowski, A. P.; MaloneyHuss, K. E. Tetrahedron Lett. 1985, 26, 5759. (c) Prashad, M.; Fraser-Reid, B. J. Org. Chem. 1985, 50, 1564. (d) Crimmins, M. T.; Lever, J. G. Tetrahedron Lett. 1986, 27, 291. (e) Ireland, R. E.; Obrecht, D. M. Helv. Chim. Acta 1986, 69, 1273. (f) Hanessian, S.; Beaulieu, P.; Dube, D. Tetrahedron Lett. 1986, 27, 5071. (g) Barrett, A. G. M.; Capps, N. K. Tetrahedron Lett. 1986, 27, 5571. (h) Jung, M. E.; Street, L. H.; Usui, Y. J. Am. Chem. Soc. 1986, 108, 6810. (i) Ardisson, J.; Ferezou, J. P.; Julia, M.; Pancrazi, A. Tetrahedron Lett. 1987, 28, 2001
    • (1984) J. Am. Chem. Soc , vol.106 , pp. 8327
    • Jung, M.E.1    Street, L.J.2
  • 19
    • 0003029135 scopus 로고
    • For a discussion of this distinction, see
    • For a discussion of this distinction, see: Danishefsky, S. J. Aldrichchimica Acta 1986, 19, 59
    • (1986) Aldrichchimica Acta , vol.19 , pp. 59
    • Danishefsky, S.J.1
  • 21
    • 0023621922 scopus 로고
    • Kay, I. T.; Williams, E. G. Tetrahedron Lett. 1983, 24, 5915. (c) Kay, I. T.; Bartholomew, D. Tetrahedron Lett. 1984, 25, 2035. (d) Armistead, D. M.; Danishefsky, S. J. Tetrahedron Lett. 1987, 28, 49
    • Wincott, F. E.; Danishefsky, S. J.; Schulte, G. Tetrahedron Lett. 1987, 28, 4951. (b) Kay, I. T.; Williams, E. G. Tetrahedron Lett. 1983, 24, 5915. (c) Kay, I. T.; Bartholomew, D. Tetrahedron Lett. 1984, 25, 2035. (d) Armistead, D. M.; Danishefsky, S. J. Tetrahedron Lett. 1987, 28, 49
    • (1987) Tetrahedron Lett , vol.28 , pp. 4951
    • Wincott, F.E.1    Danishefsky, S.J.2    Schulte, G.3
  • 22
    • 0001349508 scopus 로고
    • Danishefsky, S. J.; Bednarski, M. D. Tetrahedron Lett. 1985, 26, 3411
    • Danishefsky, S. J.; Bednarski, M. D. J. Am. Chem. Soc. 1986, 108, 7060. (b) Danishefsky, S. J.; Bednarski, M. D. Tetrahedron Lett. 1985, 26, 3411
    • (1986) J. Am. Chem. Soc , vol.108 , pp. 7060
    • Danishefsky, S.J.1    Bednarski, M.D.2
  • 23
    • 0023589262 scopus 로고
    • For a previous communication of these results, see Danishefsky, S. J.; Selnick, H. G.; Armistead, D. M.; Wincott, F. E. J. Am. Chem. Soc. 1987, 109, 8119
    • For a previous communication of these results, see: (a) Danishefsky, S. J.; Armistead, D. M.; Wincott, F. E.; Selnick, H. G.; Hungate, R. J. Am. Chem. Soc. 1987, 109, 8117. (b) Danishefsky, S. J.; Selnick, H. G.; Armistead, D. M.; Wincott, F. E. J. Am. Chem. Soc. 1987, 109, 8119
    • (1987) J. Am. Chem. Soc , vol.109 , pp. 8117
    • Danishefsky, S.J.1    Armistead, D.M.2    Wincott, F.E.3    Selnick, H.G.4    Hungate, R.5
  • 39
    • 0001343097 scopus 로고
    • Keck, G. E.; Abbott, D. E.; Boden, E. P.; Enholm, E. J. Tetrahedron Lett. 1984, 25, 3927
    • Danishefsky, S. J.; DeNinno, M. P.; Phillips, G. P.; Zelle, R. E.; Lartey, P. A. Tetrahedron 1986, 42, 2809. (b) Keck, G. E.; Abbott, D. E.; Boden, E. P.; Enholm, E. J. Tetrahedron Lett. 1984, 25, 3927
    • (1986) Tetrahedron , vol.42 , pp. 2809
    • Danishefsky, S.J.1    DeNinno, M.P.2    Phillips, G.P.3    Zelle, R.E.4    Lartey, P.A.5
  • 42
    • 0000282696 scopus 로고
    • Itoh, A.; Ozawa, S.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1981, 54, 274
    • Itoh, A.; Ozawa, S.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1980, 21, 361, (b) Itoh, A.; Ozawa, S.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1981, 54, 274
    • (1980) Tetrahedron Lett , vol.21 , pp. 361
    • Itoh, A.1    Ozawa, S.2    Oshima, K.3    Nozaki, H.4
  • 50
    • 0022517883 scopus 로고
    • The material was replenished at this stage with compound provided by degradation of naturally occuring avermectin. cf
    • The material was replenished at this stage with compound provided by degradation of naturally occuring avermectin. cf.: Hanessian, S.; Ugolini, A.; Hodges, P.; Dube, D. Tetrahedron Lett. 1986, 27, 2699
    • (1986) Tetrahedron Lett , vol.27 , pp. 2699
    • Hanessian, S.1    Ugolini, A.2    Hodges, P.3    Dube, D.4


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