Stereoselective synthesis of 2,3,4-trisubstituted tetrahydrofurans

Tetrahedron Letters

Volumn 39, Issue 45, 1998, Pages 8195-8198

  Angle, Steven R ^a   Bemier, Daniel S ^a   Chann, Keith ^a   Jones, Darin E ^a   Kim, Musong ^a   Neitzel, Martin L ^a   White, Stephen L ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0032487897     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01873-5     Document Type: Article

References (12)

1. 1. (a) Evans, D. A.; Ratz, A. M.; Huff, B. E.; Sheppard, G. S. J. Am. Chem. Soc. 1995, 117, 3448-3467.
2. (b) Kang, S. H.; Lee, S. B. Tetrahedron Lett. 1995, 36, 4089-4092, and references cited therein.
3. (c) Postema, M. H. D. C-Glycoside Synthesis; CRC Press: Boca Raton, 1995, pp 379.
4. 2. For recent examples and leading references see: (a) Zhang, H. P.; Seepersaud, M.; Seepersaud, S.; Mootoo, D. R. J. Org. Chem. 1998, 63, 2049-2052.
5. (b) Marshall, J. A.; Jiang, H. J. Tetrahedron Lett. 1998, 39, 1493-1496.
6. (c) Craig, D; King, N. P.; Shaw, A. N. Tetrahedron Lett. 1997, 38, 8599-8602.
7. (d) Petasis, N. A.; Lu, S.-P. J. Am. Chem. Soc. 1995, 117, 6394-6395.
8. (e) Zhao, Y.; Beddoes, R. L.; Quayle, P. Tetrahedron Lett. 1994, 35, 4187-4188.
9. 3. Angle, S. R.; Wei, G. P.; Ko, Y. K.; Kubo, K. J. Am. Chem. Soc. 1995, 117, 8041-8042.
10. 4. Angle, S. R.; Bernier, D. S.; El-Said, N. A.; Jones, D. E.; Shaw, S. Z. Tetrahedron Lett. 1998, 39, 3919-3922.
11. 2 (1-0 and 0.2 equiv.); the stereoselectivity and yield remained unchanged.
12. 6. This interesting stereochemical ambiguity is currently under investigation.