Improved synthesis of functionalized podand ionophores

Journal of Organic Chemistry

Volumn 61, Issue 2, 1996, Pages 775-777

  Burger, Matthew T ^a   Still, W Clark ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IONOPHORE; TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030066918     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9515438     Document Type: Article

References (16)

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2. (b) Armstrong, A.; Still, W. C. J. Org. Chem. 1992, 57, 4580-4582.
3. (c) Wang, X.; Erickson, S. D.; Iomori, T.; Still, W. C. J. Am. Chem. Soc. 1992, 114, 4128-4137.
4. Semmelhack, M. F.; Kim, C. R.; Dobler, W ; Meier, M. Tetrahedron Lett. 1989, 30, 4925-4928.
5. The procedure for the preparation of the enantjomer of 6 was followed Li, Ge, Ph.D. Thesis, Columbia University, 1993, p 92.
6. Danishefsky, S. J.; Wan, C F. Synth. Commun. 1978, 8 (4), 211-218.
7. Danishefsky, S. J.; Pearson, W. H., Harvey, D. F.; Maring, C. J.; Springer, J. P. J. Am. Chem. Soc. 1985, 107, 1256-1268.
8. Reetz, M. T.; Gansauer, A. Tetrahedron 1993, 49, 6025-6030. Commercially available (Aldrich) lithium perchlorate was dried under high vacuum at 180 °C for 48 h.
9. Damshefsky, S.; Kitahara, T.; Yan, C. F.; Morris, J. J. Am. Chem. Soc. 1979, 101, 6996-7000
10. Danishefsky, S. J.; Larson, E.; Askin, D.; Kato, M. J. Am. Chem. Soc 1985, 107, 1246-1255.
11. Commercially available (Aldrich) 90% tech grade 1-methoxybut-1-en-3-one was distilled prior to use.
12. (a) Hills, P. R.; McQuillan, F. J. Chem. Soc. 1953, 4060-4065.
13. (b) Harayama, T.; Cho, H.; Inubushi, Y. Chem. Pharm. Bull. 1978, 26(4), 1201-1214.
14. Griffith, W. F.; Ley, S. V.; Whitcombe, G. P.; White, A. D. Chem. Commun. 1987, 1625-1627.
15. Danishefsky, S. J.; Myles, D. C.; Harvey, D. F. J. Am. Chem. Soc. 1987, 109, 862-867.
16. 3 was prepared as described in Yamaka, J.; Ando, T. Chem. Lett. 1979, 755-758.