Studies in Spiroketal Synthesis 1. Nucleophilic Addition to an Oxy-Stabilized Carbonium Ion Generated on a 1,7-Dioxaspiro[5.5]undecane Ring System

Synlett

Volumn 1996, Issue 11, 1996, Pages 1063-1064

  Mead, Keith T ^a   Zemribo, Ronald ^a  

^a MISSISSIPPI STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003038177     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5687     Document Type: Article

References (17)

1. For a review of synthetic methods, see: Kluge, A. F. Heterocycles 1986, 24, 1699-1740.
2. For example, see: Stolze, D. A.; Sierra, F, P.; Heeg, M. J.; Albizati, K. F. Tetrahedron Lett. 1991, 33, 4081-4084.
3. For an example, see: Holmes, C. P.; Bartlett, P. A. J. Org.Chem. 1989, 54, 98-108.
4. Oikawa, M.; Ueno, T.; Oikawa, H.; Ichihara, A. J. Org. Chem. 1995, 60, 5048-5068, and references cited therein.
5. Ireland, R. E.; Haebich, D. Chem. Ber. 1981, 114(4), 1418-1427.
6. Hydride addition has been reported, although an oxy - stabilized intermediate was not proposed by the authors. For details, see: Barrett, A. G. M.; Carr, R. A. E.; Finch, M.A.W.; Florent, J.-C.; Richardson, G.; Walshe, N. D. A. J. Org. Chem. 1986, 51, 4254-4260.
7. (a) Kobayashi, M.; Aoki, S.; Kitagawa, I. Tetrahedron Lett. 1994, 35, 1243-1246;
8. (b) Pettit, G. R.; Cichacz, Z. A.; Gao, F.; Herald, C. L.; Boyd, M. R. J. Chem. Soc., Chem. Commun. 1993, 1166-1168.
9. Synthesis of aldehyde 1 began with a Suzuki coupling between the enol inflate of cyclopentanone and the THP ether of 3- buten-1-ol (82%). Alcohol deprotection (p-TsOH, MeOH) and Swem oxidation (86% two steps) gave aldehyde 1.
10. Brady, W. T.; Saidi, K. J. Org. Chem. 1979, 44, 733-737.
11. 3, 75 MHz) δ 17.68, 18.60, 30.58, 30.62, 34.72, 34.80, 41.10, 51.48, 56.12, 66.58, 97.82, 98.10, 171.95.
12. 3, 75 MHz) δ 17.9, 18.5, 30.5, 30.7, 35.0, 35.1, 40.7, 41.0, 56.2, 66.4, 69.2, 97.7, 116.4, 135.3, 171.8.
13. 3, 75 Hz) δ 17.9, 18.5, 30.6, 30.8, 34.8, 34.9, 41.2, 56.2, 66.4, 73.1, 79.2, 86.4, 97.0, 171.9. For HRMS data of the corresponding acid, see Mead, K.T.; Zemribo, R. Synlett 1996, 1065.
14. 3), 75 MHz) δ 18.5, 18.6, 30.1, 30.7, 35.1, 35.7, 41.3, 56.1, 66.3, 67.0, 97.2, 172.0.
15. (a) Evans, D. A.; Sacks, C. E.; Whitney, R. A.; Mandel, N. G. Tetrahedron Lett. 1978, 727-730.
16. (b) Nakahara, Y.; Fujita, A.; Ogawa, T. Agric. Biol. Chem. 1987, 51, 1009-1015.
17. Perkins, M. V.; Jacobs, M. F.; Kitching, W.; Cassidy, P.;Lewis, J. A.; Drew, R. A. I. J. Org. Chem. 1992, 57, 3365-3380.