Cis- and trans-1,7,9-trioxadispiro[5.1.5.3]hexadecane: Stability studies and solution structures

Tetrahedron Letters

Volumn 37, Issue 31, 1996, Pages 5465-5468

  McGarvey, Glenn J ^a   Stepanian, Marshall W ^a   Bressette, Andrew R ^a   Ellena, Jeffrey F ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SPIRO COMPOUND; TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; DRUG STABILITY; DRUG STRUCTURE; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0030605819     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01166-5     Document Type: Article

References (15)

1. 1. See previous Communication.
2. 2. For a recent review on spiroketal synthesis see: Vaillancourt, V.; Pratt, N.E.; Perron, F.; Albizati, K.F. The Total Synthesis of Natural Products 1992, 8, 533-691.
3. 3. For an earlier study on these bis-spiroketals: Brimble, M.A.; Rush, C.J. J. Chem. Soc. Perk. Trans. 1 1994, 497-500, and references cited therein.
4. 4. For extensive reviews on these stereoelectronic effects: (a) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon Press: Oxford, 1983.
5. (b) Juaristi, E.; Cuevas, G. The Anomeric Effect, CRC Press: Boca Raton, 1995.
6. 2O/hexanes) and HPLC.
7. 6. Gordon, A.J.; Ford, R.A. The Chemist's Companion, John Wiley and Sons: New York, 1972.
8. 7. Pothier, N.; Rowan, D.D.; Deslongchamps, P.; Saunders, J.K. Can. J. Chem. 1981, 59, 1132-1139.
9. 8. This compound was prepared by the method previously reported: Amouroux, R. Heterocycl. 1984, 22, 1489-1492.
10. 9. Hull, W.E. in Methods in Stereochemical Analysis: Two-Dimensional NMR Spectroscopy, Applications for Chemists and Biochemists; Carlson, R.M.; Croasmun, W.R., eds.; VCH Publishers, Inc.: New York, 1987; Vol. 9, Chap. 2.
11. 10. Bax, A.; Subramanian, S. J. Magn. Reson. 1986, 67, 565-569.
12. 11. Bax, A.; Davis, D.G. J. Magn. Reson. 1985, 65, 355-360. This technique proved especially useful for the establishment of connectivities of the independent spin systems found in this class of compounds.
13. gem=12.6 Hz.
14. 14 derivatives.
15. 14. Stepanian, M.W.; McGarvey, G.J., unpublished data.