The effect of varying substituents on the equilibrium distribution and conformation of macrocyclic steroidal N-acyl hydrazones

Organic Letters

Volumn 2, Issue 10, 2000, Pages 1435-1438

  Simpson, Mark G ^a   Watson, Stephen P ^b   Feeder, Neil ^a   Davies, John E ^a   Sanders, Jeremy K M ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001692105     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005754x     Document Type: Article

References (15)

1. (a) Still, W. C.; Hauck, P.; Kempf, D. Tetrahedron Lett. 1987, 25, 2817-2820.
2. (b) Hioki, H.; Still, W. C. J. Org. Chem. 1998, 63, 904-905.
3. (c) Lehn, J.-M. Chem. Eur. J. 1999, 5, 2455-2463.
4. (d) Brady, P. A.; Sanders, J. K. M. J. Chem. Soc., Perkin Trans. 1 1997, 3237-3253.
5. (e) Calama, M. C.; Timmerman, P.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2000, 39, 755-758.
6. Hockless, D. C. R.; Lindoy, L. F.; Swiegers, G. F.; Wild, S. B. J. Chem. Soc., Perkin Trans. 1 1998, 117-122.
7. Cousins, G. R. L.; Poulsen, S.-A.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1999, 16, 1575-1576.
8. Davis, A. P. Chem. Soc. Rev. 1993, 22, 243-253.
9. Bonar-Law, R. P.; Sanders, J. K. M. J. Am. Chem. Soc. 1995, 117, 259-271.
10. Brady, P. A.; Bonar-Law, R. P.; Rowan, S. J.; Suckling, C. J.; Sanders, J. K. M. J. Chem. Soc. Chem. Commun. 1996, 319-320.
11. Lenman, M. M.; Lewis, A.; Gani, D. J. Chem. Soc., Perkin Trans. 1 1997, 2297-2311.
12. Gordon, M. S.; Krause, J. G.; Linneman-Mohr, M. A.; Parchue, R. R. Synthesis 1980, 244-245.
13. Palla, G.; Predieri, G.; Domiano, P.; Vignali, C.; Turner, W. Tetrahedron 1986, 42, 3649-3654.
14. Ercolani, G.; Mandolini, L.; Mencarelli, P.; Roelens, S. J. Am. Chem. Soc. 1993, 115, 3901-3908.
15. The behavior of steroid-based hydrazides contrasts markedly with amino acid-based hydrazides. In the case of amino acid-based monomers, a wide range of macrocycles were formed at equilibrium according to ESI-MS. See ref 3 for more details.