Synthesis of tetrahydrofurans from protected β-hydroxyaldehydes: Optimization of the alcohol protecting group

Tetrahedron Letters

Volumn 39, Issue 23, 1998, Pages 3919-3922

  Angle, Steven R ^a   Bernier, Daniel S ^a   El Said, Nahla A ^a   Jones, Darin E ^a   Shaw, Stephanie Z ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALDEHYDE; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 0032482504     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00720-5     Document Type: Article

References (18)

1. 1. Angle, S. R.; Wei, G. P.; Ko, Y. K.; Kubo, K. J. Am. Chem. Soc. 1995, 117, 8041-8042.
2. 2. (a) Womack, E. B.; Nelson, A. B. Org. Synth. Coll. Vol. III 1955, 392-393.
3. (b) Prepared by modification of following procedure: Searle, N.E. Org. Synth. Coll. Vol. IV 1963, 424-426.
4. 3. Angle, S. R.; Boyce, J. P. Tetrahedron Lett. 1994, 35, 6461-6464.
5. 4. (a) Corey, E. J.; Snider, B. B. J. Am. Chem. Soc. 1972, 94, 2549-2550.
6. (b) Corey, E. J.; Cho, H.; Rucker, C.; Hua, D. H. Tetrahedron Lett. 1981, 22, 3455-3458.
7. 5. (a) Mancuso, A. J.; Swern, D. Synthesis, 1981, 165-185.
8. (b) Tidwell, T. T. Synthesis, 1990, 857-870.
9. 6. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis, 1994, 639-666.
10. 7. (a) For preparation of Dess-Martin periodinane see: Ireland R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
11. (b) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156.
12. 3) in 0.7% yield. Attempts to improve the yield by other oxidation methods failed.
13. 13C NMR, IR, MS, and HRMS.
14. 10. Formation of the β-keto ester is due to a competitive Roskamp homologation, see: (a) Holmquist, C. R.; Roskamp, E. J. J. Org. Chem. 1989, 54, 3258-3260.
15. (b) Holmquist, C. R.; Roskamp, E. J. Tetrahedron Lett. 1992, 33, 1131-1134.
16. 4) and concentration afforded crude product(s). Flash chromatography on silica gel (ethyl acetate or ethyl ether/hexane mixtures) gave product(s) in the yields shown.
17. 12. The stereochemistry of 7 was assigned based on coupling constant correlation to a previously reported ethyl ester derivative, see reference 1.
18. 13. Stereochemistry of 9 was determined by reduction to the diol and comparison of the spectral data with those reported in the literature: Placec, J.; Tong, W.; Chattopadhyaya, J. J. Am. Chem. Soc. 1993, 115, 9734-9746.