Synthesis of threo- and erythro-bis(2,2'-tetrahydrofuran). A novel serendipitous synthesis of a spiroketal

Tetrahedron Letters

Volumn 40, Issue 11, 1999, Pages 2209-2212

  Kelly, David R ^a   Nally, James ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,6 DIOXASPIRO[4.5]DECANE; BIS(2,2' TETRAHYDROFURAN); SILVER; TETRAFLUOROBORATE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CYCLIZATION; ISOMERISM; RACEMIC MIXTURE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033548583     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00173-2     Document Type: Article

References (26)

1. Shimizu, Y.; Bando, H.; Chou, H.-N.; Van Duyne, G.; and Clardy, J. C. J. Chem. Soc., Chem. Commun., 1986, 1656-1658.
2. For reviews see Kelly, D. R. in The Chemistry of Natural Products, Thompson, R. H. (ed), Blackie, Glasgow, 2nd edition, 1993, 382-441;
3. Elliot, M. C. Contemp. Org. Synth. 1997, 4, 238- 259 and reference 10 below.
4. c.f. Alder, R. W.; Miller, A. J.; Rushbrook, D. I. J. Chem. Soc., Chem. Commun. 1989, 277-279.
5. Bartlett, P. A.; Mori, I. and Bose, J. A. J. Org. Chem. 1989, 54, 3236-3239.
6. Nakata, T.; Nomura, S.; Matsukura, H. and Morimoto, M. Tetrahedron Lett. 1996, 37, 217-220;
7. Nakata, T.; Schmid, G.; Vranesic, B.; Okigawa, M.; Smith-Palmer, T.; Kishi, Y. J. Am. Chem. Soc. 1978, 100, 2933-2935.
8. See Octahydro-(2,2′)bifuranyl, Beilstein registry no. 104583, Chem. Abstr. registry nos. [1592-33- 2], [90334-38-6], [90334-40-0].
9. e.g. Gevorgyan, V.; Priede, E.; Liepins, E.; Gavars, M.; Lukevics, E. J. Organomet. Chem., 1990, 595, 333-338.
10. Dana, G.; Girault, J.-P. Bull. Chem. Soc. Fr. 1972, 1650-1656.
11. Nakayama, K. Diss. Abstr. Int. B 1986, 47, 1562;
12. Chem. Abst. 1986, 706, 67029s.
13. Hayashi, H.; Fujiwara, K.; Murai, A. Tetrahedron 1997, 53, 12425-12468.
14. Odaira, Y.; Matsuo, H.; Sakakibara, T.; Tsutsumi, S. Nippon Kagaku Zasshi 1967, 88, 39-42;
15. Chem. Abstr. 1967, 67, 2591a.
16. Naarmann, H.; Zdenek, J.; Veihe, H. G.; Beaujean, M. and Merenyi, R. Ger. Offen. 1981, 29 29 250;
17. Naarmann, H.; Beaujean, M.; Merenyi, R. and Veihe, H. G., Polymer Bull. 1980, 2, 363-372, 417-425.
18. 2 axis and the erythro-stereoisomer 5 a plane of symmetry.
19. Nagarkatti, J. P. and Ashley, K. R. J. Ind. Chem. Soc. 1976, 53, 666-669;
20. Nagarkatti, J. P. and Ashley, K. R. Tetrahedron Lett. 1973, 4599-4600.
21. Tolstikov, G. A.; Odinokov, V. N.; Galeeva, R. I. and Bakeeva, R. S. Tetrahedron Lett. 1978, 1857-1858.
22. Hanessian, S.; Thavonekham, B. and Dehoff, B. J. Org. Chem. 1989, 54, 5831-5833.
23. Fletcher, M. T. and Kitching, W. Chem. Rev. 1995, 95, 768-828;
24. Perron, F. and Albizati, K. F. Chem. Rev. 1989, 89, 1617-1661.
25. This material was identical to an authentic sample of the spiroketal which was kindly provided by Prof. Witko Francke. Francke, W.; Reith, W.; Sinnwell, V. Chem. Ber. 1980, 113, 2686-2693.
26. Nishiyama, H.; Naritomi, T.; Sakuta, K. and Itoh, K. J. Org. Chem. 1983, 48, 1557-1559.