Syn-oxidative cyclizations of trishomoallylic alcohols: Stereoselective and stereospecific synthesis of trans-tetrahydropyranyl alcohols

Tetrahedron Letters

Volumn 38, Issue 44, 1997, Pages 7683-7686

  McDonald, Frank E ^a   Singhi, Aatur D ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; TETRAHYDROPYRANYL ALCOHOL DERIVATIVE; TRISHOMOALLYLIC ALCOHOL DERIVATIVE; UNCLASSIFIED DRUG;

ALCOHOL METABOLISM; ARTICLE; CYCLIZATION; EPOXIDATION; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030696605     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10005-3     Document Type: Article

References (15)

1. Reviews: (a) Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, pp 411-454.
2. (b) Boivin, T. L. B. Tetrahedron 1987, 43, 3309.
3. (c) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321.
4. (d) Harding, K. E.; Tiner, T. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: New York, 1991; Vol. 4, pp. 363-421.
5. (a) Cr: McDonald, F. E.; Towne, T. B. J. Am. Chem. Soc. 1994, 116, 7921, and reference 7 therein.
6. (b) Mn: Brown, R. C. D.; Kocienski, P. J. Synlett 1994, 415, and references therein.
7. (c) Ru: Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
8. (d) Re: Sinha, S. C.; Sinha, A.; Yazbak, A.; Keinan, E. J. Org. Chem. 1996, 61, 7640, and references therein.
9. Kennedy, R. M.; Tang, S. Tetrahedron Lett. 1992, 33, 3729.
10. Sinha, S. C.; Sinha-Bagchi, A.; Keinan, E. J. Am. Chem. Soc. 1995, 117, 1447.
11. (a) McDonald, F. E.; Towne, T. B. J. Org. Chem. 1995, 60, 5750.
12. (b) Towne, T. B.; McDonald, F. E. J. Am. Chem. Soc. 1997, 119, 6022.
13. 3N (70%); (b) EtMgBr, THF (90%)
14. 2: C, 68.30; H, 11.47. Found: C, 67.72; H, 11.54.
15. 4, diglyme, 160°C (45%).