A novel route to monoanomeric spiroketals

Tetrahedron Letters

Volumn 39, Issue 23, 1998, Pages 3891-3894

  Zemribo, Ronald ^a   Mead, Keith T ^a  

^a MISSISSIPPI STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; DIASTEREOISOMER; NUCLEAR OVERHAUSER EFFECT; STEREOCHEMISTRY; SYNTHESIS; THERMODYNAMICS;

EID: 0032482480     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00685-6     Document Type: Article

References (16)

1. 1. Kobayashi, M.; Aoki, S.; Kitagawa, I. Tetrahedron Lett. 1994, 35, 1243-1246.
2. 2. 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, 1302-1304.
3. 3. Fusetani, N.; Shinoda, K.; Matsunaga, S. J. Am. Chem. Soc. 1993, 115, 3977-3981.
4. 4. (a) Hayes, C. J.; Heathcock, C. H. J. Org. Chem. 1997, 62, 2678-2679.
5. (b) Paquette, L. A.; Braun, A. Tetrahedron Lett. 1997, 38, 5119-5122.
6. (c) Smith, III, A. B.; Zhuang, L.; Brook C. S.; Lin, Q.; Moser, W. H.; Trout, R. E. L.; Boldi, A. M. Tetrahedron Lett. 1997, 38, 8671-8674.
7. (d) Paterson, I.; Wallace, D. J.; Gibson, K. R. Tetrahedron Lett. 1997, 38, 8911-8914.
8. 5. Mead, K. T.; Zemribo, R. SynLett 1996, 1063-1064.
9. 6. Zemribo, R.; Romo, D. Tetrahedron Lett. 1995, 36, 4159-4162.
10. 7. White, D.; Zemribo, R.; Mead, K. T. Tetrahedron Lett. 1997, 38, 2223-2226.
11. 8. A general route to spirolactols has since been developed in our lab, in which cyclopentene ozonolysis is conducted in the presence of the free alcohol (see below). (Equation Presented)
12. 9. We have since found a direct route to methyl acetals from spirolactols (see below). (Equation Presented)
13. 10. During the course of this work, a similar equilibrium mixture of spiroketals, prepared by acid-catalyzed ring closure of an open-chain keto-diol, was reported by Heathcock and Hayes. See: reference 4a.
14. 11. For a mechanistic explanation for the formation of tetrahydropyran 13 from 2c, see reference 5.
15. 3, 75 MHz) δ 14.19, 19.14, 29.69, 30.84, 34.83, 37.61, 38.51, 40.82, 45.02, 61.67, 64.35, 68.85, 69.51, 97.97
16. 13. See the following paper in this issue.