Cis- and trans-1,7,9-trioxadispiro[5.1.5.3]hexadecane: Synthetic studies

Tetrahedron Letters

Volumn 37, Issue 31, 1996, Pages 5461-5464

  McGarvey, Glenn J ^a   Stepanian, Marshall W ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SPIRO COMPOUND; TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030605886     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01165-3     Document Type: Article

References (21)

1. 1. (a) Deslongchamps, P.; Rowan, D.D.; Pothier, N.; Sauvé, G.; Saunders, J.K. Can. J. Chem. 1981, 59, 1105-1121,
2. (b) Pothier, N.; Rowan, D.D.; Deslongchamps, P. Saunders, J.K. Can. J. Chem. 1981, 59, 1132-1139.
3. (c) Deslongchamps, P.; Pothier, N. Can. J. Chem. 1990, 68, 597-603.
4. 2. For an extensive discussion see: Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon Press: Oxford, 1983.
5. 3. For a review see: Vaillancourt, V.; Pratt, N.E.; Perron, F.; Albizati, K.F. The Total Synthesis of Natural Products 1992, 8, 533-691.
6. 4. Brimble, M.A.; Rush, C.J. J. Chem. Soc. Perk. Trans. 1 1994, 497-500.
7. 5. Amouroux, R. Heterocycl. 1984, 22, 1489-1492.
8. 3I as the electrophile.
9. 7. (a) Huckin, S.N.; Weiler, L. J. Am. Chem. Soc. 1974, 96, 1082-1087.
10. (b) Heary, A.P.; Parsons. P.J.; J. Chem. Soc., Chem. Commun. 1989, 1090-1091.
11. 2, 0°C→25°C (66%); (c) NaI, acetone, 80°C (75%).
12. 9. Helquist, P.; Iyer, R.S.; McCanna, T.D.; Nystrom, J. Tetrahedron Lett. 1985, 26, 5393-5396.
13. 10. Elsinger, F. Org. Synth. 1965, 45, 7.
14. 4I: (a) Bailey, W.F.; Punzalan, E.R. J. Org. Chem. 1990, 55, 5404-5406.
15. (b) Negishi, E.; Rousset, C.J.; Swanson, D.R. J. Org. Chem. 1990, 55, 5406-5409.
16. 12. Posner, G.H.; Shulman-Roskes, E.M.; Oh, C.H.; Carry, J.-C.; Green, J.V.; Clark, A.B.; Dai, H.; Anjeh, T.E.N. Tetrahedron Lett. 1991, 32, 6489-6492.
17. 13. Crooks, S.L.; Shearer, B.G.; Marshall, J.A. J. Org. Chem. 1987, 52, 1236-1245.
18. 14. For this method of nitrile oxide generation: Torssell, K.B.G.; Larsen, K.E. Tetrahedron 1984, 40, 2985-2988.
19. 15. Bloom, J.D.; Schow, S.R.; Smith, A.B.; Thompson, A.S.; Winzenberg, K.N. J. Am. Chem. Soc. 1986, 108, 2662-2674.
20. 16. Curran, D.P. J. Am. Chem. Soc. 1983, 105, 5826-5833.
21. 17. Vedejs, E.; Fuchs, P.L. J. Org. Chem. 1971, 36, 366-367.