Enantiospecific synthesis of the spiroacetal moieties of avermectins A1b, B1b, A1a, B1a, A2b, B2b, A2a, and B2a and milbemycins α7 and α8

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 1, 1988, Pages 85-97

  Baker, Raymond ^a,b   Head, John C ^a   Swain, Christopher J ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^b NEUROSCIENCE RESEARCH CENTRE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010419553     PISSN: 14727781     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19880000085     Document Type: Article

References (25)

1. G. Albers-Schonberg, B. H. Arison, J. C. Chabala, A. W. Douglas, P. Eskola, M. H. Fisher, J. M. Hirshfield, K. Hoogsteen, A. Lusi, H. Mrozik, J. K. Smith, J. P. Springer, and R. L. Tolman, Interscientific Conference on Antimicrobial Agents and Chemotherapy, 1978, Abstract No. 464
2. G. Albers-Schonberg, B. H. Arizon, J. C. Chabala, A. W. Douglas, P. Eskola, M. H. Fisher, A. Lusi, H. Mrozik, J. L. Smith, and R. L. Tolman, J. Am. Chem. Soc., 1981, 103, 4216
3. J. P. Springer, B. H. Arison, J. M. Hirshfield, and K. Hoogsteen, J. Am. Chem. Soc., 4221.
4. R. W. Burg, B. M. Miller, E. E. Baker, J. Birnbaum, S. A. Currie, R. Hartman, Y. L. Kong, R. L. Monaghan, G. Olson, I. Putter, J. B. Tunac, H. Wallick, E. O. Stapley, R. Oiwa, and S. Omura, Antimicrob. Agents Chemother., 1979, 15, 361.
5. J. C. Chabala, H. Mrozik, R. L. Tolman, P. Eskola, A. Lusi, L. H. Peterson, M. F. Woods, and M. H. Fisher, J. Med. Chem., 1980, 23, 1134.
6. E. W. Cupp, M. J. Bernado, A. E. Kiszewski, R. C. Collins, H. R. Taylor, M. A. Aziz, and B. M. Greene, Science, 1986, 231, 740.
7. M. H. Fisher, ‘The Avermectins,’ in Recent Adv. Chem. of Insect Control., 1985, 53.
8. H. Mishma, M. Kurabayashi, and C. Tamura, Tetrahedron Lett., 1975, 711.
9. Y. Takiguchi, K. Mishma, M. Okuda, M. Terao, A. Aoki, and R. Fukunda, J. Antibiot., 1980, 33, 1120.
10. A. B. Smith, III, S. R. Schow, J. D. Bloom, A. S. Tompson, and K. N. Winzenberg, J. Am. Chem. Soc., 1982, 104, 4015.
11. D. R. Williams, B. A. Barner, K. Nishitani, and J. G. Phillips, J. Am. Chem. Soc., 1982, 104, 4708.
12. P. Kocienski and S. D. A. Street, J. Chem. Soc., Chem. Commun., 1984, 571.
13. R. Baker, R. H. O. Boyes, D. M. P. Broom, J. A. Devlin, and C. J. Swain, J. Chem. Soc., Chem. Commun., 1983, 830.
14. S. V. Atwood, A. G. M. Barrett, and J.-C. Florent, J. Chem. Soc., Chem. Commun., 1981, 556.
15. C. Greek, P. Grice, S. V. Ley, and A. Wonnacott, Tetrahedron Lett., 1986, 27, 5277.
16. S. Hanessian, A. Ugolini, and M. Therien, J. Org. Chem., 1983, 48, 4427.
17. R. Baker, J. C. Head, and C. J. Swain, J. Chem. Soc., Chem. Commun., 1985, 309.
18. M. Hirama, T. Nakamine, and S. Ito, Tetrahedron Lett., 1986, 27, 5281.
19. R. Baker, R. H. O. Boyes, D. M. P. Broom, M. J. O’Mahony, and C. J. Swain, J. Chem. Soc., Perkin Trans. 1, 1987, 1613.
20. R. Baker, M. J. O’Mahony, and C. J. Swain, J. Chem. Soc., Perkin Trans. 1, 1987, 1623.
21. D. K. Murphy, R. L. Alumbaugh, and B. Rickborn, J. Am. Chem. Soc., 1969, 91, 2649.
22. D. A. Evans, M. D. Ennis, and D. J. Mathre, J. Am. Chem. Soc., 1982, 104, 1737.
23. L. F. Hatch and T. P. Li, J. Org. Chem., 1963, 28, 2400.
24. A. I. Meyers, G. Knaus, K. Kamata, and M. E. Ford, J. Am. Chem. Soc., 1976, 98, 567.
25. Heilbron’s ‘Dictionary of Organic Compounds,’ 1985, 4, 3884.