Synthesis and stereochemical elucidation of a 14-membered ring phosphonate

Organic Letters

Volumn 3, Issue 5, 2001, Pages 643-646

  Pungente, Michael D ^a   Weiler, Larry ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013402299     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006422v     Document Type: Article

References (15)

1. Smith, A. B., III; Leahy, J. W.; Noda, I.; Remiszewski, S. W.; Liverton, N. J.; Zibuck, R. J. Am. Chem. Soc. 1992, 114, 2995.
2. Mitsunobu, O. Synthesis 1981, 1.
3. Campbell, D. A. J. Org. Chem. 1992, 57, 6331.
4. Jones, G. H.; Hamamura, E. K.; Moffatt, J. G. Tetrahedron Lett. 1968, 5731.
5. 3P (368 mg, 1.40 mmol), followed by DEAD (221 μL, 1.40 mmol). After 2 h, the solvent was removed under reduced pressure, and the resulting crude mixture was purified by flash chromatography using 2:1 hexane and ethyl acetate to afford the separated diastereomers, 10a and 10b, in a 5:1 ratio based on recovered yields and a combined yield of 82%. In addition, 6 mg of dimer 11 was isolated as a colorless, crystalline solid.
6. 2: C, 67.42; H, 9.24. Found: C, 67.51; H, 9.28.
7. 3; Z = 2; colorless; T = 294 K; R = 0.030; GOF = 2.27.
8. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
9. Burkert, U.; Allinger, N. L. ACS Monograph 177; American Chemical Society: Washington, DC, 1982.
10. (a) Darrow, J. W.; Drueckhammer, D. G. J. Org. Chem. 1994, 59, 2976.
11. (b) Darrow, J. W.; Drueckhammer, D. G. Bioorg. Med. Chem. 1996, 4, 1341.
12. (c) Hanessian, S.; Galéotti, N.; Rosen, P.; Oliva, G.; Babu, S. Bioorg. Med. Chem. Lett. 1994, 4, 2763.
13. (d) Harvey, T. C.; Simiand, C.; Weiler, L.; Withers, S. G. J. Org. Chem. 1997, 62, 6722.
14. (a) Gorenstein, D. G. Chem. Rev. 1987, 87, 1047.
15. (b) Chang, J. W.; Gorenstein, D. G. Tetrahedron 1987, 43, 5187.