Studies in Spiroketal Synthesis 2. A Tandem Cyclization Route to the 1,7-Dioxaspiro[5.5]undecane Ring System

Synlett

Volumn 1996, Issue 11, 1996, Pages 1065-1066

  Mead, Keith T ^a   Zemribo, Ronald ^a  

^a MISSISSIPPI STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002950790     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5688     Document Type: Article

References (19)

1. For a review of synthetic approaches to this ring system, see: Kluge, A. F. Heterocycles 1986, 24, 1699-1740.
2. For an exception, see talaromycin: Crimmins, M. T.; O'Mahony, R. J. Org. Chem. 1989, 54, 1157.
3. For previously reported routes to these structures, see: (a) Negri, D. P.; Kishi, Y. Tetrahedron Lett. 1987, 28, 1063-1066; (b) Smith, A. B.; Schow, S. R.; Bloom, J. D.; Thompson, A. S.; Winzenberg, K. J. Am. Chem. Soc. 1982, 104, 4015.
4. For previously reported routes to these structures, see: (a) Negri, D. P.; Kishi, Y. Tetrahedron Lett. 1987, 28, 1063-1066; (b) Smith, A. B.; Schow, S. R.; Bloom, J. D.; Thompson, A. S.; Winzenberg, K. J. Am. Chem. Soc. 1982, 104, 4015.
5. Altohyrtins: Kobayashi, M.; Aoki, S.; Kitagawa, I. Tetrahedron Lett. 1994, 35, 1243; Spongistatins: (a) Pettit, G. R.; Cichacz, Z. A.; Gao, F.; Herald, C. L.; Boyd, M. R.; Schmidt, J. M.; Hooper, J. N. A. J. Org. Chem. 1993, 58, 1302; (b) Pettit, G. R.; Cichazc, Z. A.; Gao, F.; Herald, C. L.; Boyd, M. R. J. Chem. Soc., Chem. Commun. 1993, 1166.
6. Altohyrtins: Kobayashi, M.; Aoki, S.; Kitagawa, I. Tetrahedron Lett. 1994, 35, 1243; Spongistatins: (a) Pettit, G. R.; Cichacz, Z. A.; Gao, F.; Herald, C. L.; Boyd, M. R.; Schmidt, J. M.; Hooper, J. N. A. J. Org. Chem. 1993, 58, 1302; (b) Pettit, G. R.; Cichazc, Z. A.; Gao, F.; Herald, C. L.; Boyd, M. R. J. Chem. Soc., Chem. Commun. 1993, 1166.
7. Altohyrtins: Kobayashi, M.; Aoki, S.; Kitagawa, I. Tetrahedron Lett. 1994, 35, 1243; Spongistatins: (a) Pettit, G. R.; Cichacz, Z. A.; Gao, F.; Herald, C. L.; Boyd, M. R.; Schmidt, J. M.; Hooper, J. N. A. J. Org. Chem. 1993, 58, 1302; (b) Pettit, G. R.; Cichazc, Z. A.; Gao, F.; Herald, C. L.; Boyd, M. R. J. Chem. Soc., Chem. Commun. 1993, 1166.
8. Mead, K. T.; Zemribo, R. Synlett 1996, 1063.
9. For previous examples of carbonyl-directed openings of β-lactones in cyclic ether synthesis, see: Mead, K. T.; Pillai, S. K. Tetrahedron Lett. 1993, 34, 6997.
10. 3, 75 MHz) δ 18.34, 18.75, 30.49, 30.70, 35.04, 35.17, 40.69, 40.95, 65.98, 69.12, 96.68, 116.47, 135.24, 175.05; FAB HRMS: no molecular ion detected.
11. 3 (M+Li): 285.2042, found: 285.2044.
12. 13C-NMR data of the corresponding methyl ester, see preceding paper in this journal.
13. 3, 300 MHz) d 1.05-1.90 (br, 12H), 3.07 (dd, 1H, J=18, 6 Hz), 4.18 (m, 1H), 4.54 (m, 1H), 4.75-4.87 (4H), 5.04 (dd, 1H, J=7, 7 Hz), 5.20 (ddd, 1H, J=7, 7, 7 Hz).
14. 5.
15. 13C-NMR data of the corresponding methyl ester, see Mead, K. T.; Zemribo, R. Synlett 1996, 1063.
16. 4. For examples, see: Oikawa, M.; Ueno, T.; Oikawa, H.; Ichihara, A. J. Org. Chem. 1995, 60, 5048, and references cited therein.
17. (a) Pommier, A.; Pons, J.-M.; Kocienski, P. J.; Wong, L. Synthesis 1994, 1294;
18. (b) Zemribo, R.; Romo, D. Tetrahedron Lett. 1995, 36, 4159.
19. Zemribo, R.; Champ, M. S.; Romo, D. Synlett 1996, 278-280.