Stereocontrolled Synthesis of D-Pentitols, 2-Amino-2-deoxy-D-pentitols, and 2-Deoxy-D-pentitols from D-Glyceraldehyde Acetonide

Journal of the American Chemical Society

Volumn 104, Issue 4, 1982, Pages 1109-1111

  Minami, Norio ^a   Ko, Soo Sung ^a   Kishi, Yoshito ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001233216     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00368a040     Document Type: Article

References (16)

1. Uemura, D.; Hirata, Y.; Naoki, H.; Iwashita, T. Tetrahedron Lett. 1981, 2781.
2. Moore, R. E.; Bartolini, G. J. Am. Chem. Soc. 1981, 103, 2491 and references cited therein.
3. D-Glyceraldehyde acetonide (1) was prepared according to the method reported by H. O. L. Fischer and E. Baer (Helv. Chim. Acta 1934, 17, 622).
4. If necessary, L-glyceraldehyde acetonide is available; for example, see: M. E. Jung and T. J. Shaw, J. Am. Chem. Soc. 1980, 102, 6304.
5. Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974.
6. The most recent contribution to this method from the Sharpless laboratory is found in: Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237; we thank Professor Sharpless for a preprint of this paper.
7. Seyferth, D.; Simmons, H. D. Jr.; Singh, G. Organomet. Chem. 1965, 3, 337.
8. Seyferth, D.; Heeren, J. K.; Singh, G.; Grim, S. O.; Hughes, W. B. J. Organomet. Chem. 1966, 5, 267.
9. 3, c 2.38)) obtained from the acetylenic route. Thus, this Wittig reaction provided a short, practical synthesis of 3: Mitra, A.; Kishi, Y., unpublished results.
10. Nagaoka, H.; Kishi, Y. Tetrahedron 1981, 37, 3873.
11. Johnson, M. R.; Kishi, Y. Tetrahedron Lett. 1979, 4347.
12. Hasan, I.; Kishi, Y. Tetrahedron Lett. 1980, 4229.
13. 3CCO. In both cases, the stereochemistry of the major epoxides correspond to that of 7. Epoxidation of 16 under the Sharpless conditions [(-BuOOH/VO(acac)2: J. Am. Chem. Soc. 1973, 95, 6136] yielded a 5.3:1.0 mixture of the two possible epoxides at room temperature in benzene and a 3.4:1.0 mixture at −23 °C in toluene. The stereochemistry of the major epoxide correponds to that of 7.
14. Epoxide ring opening of a system somewhat similar to this is known; for example, see: Corey, E. J.; Hopkins, P. B.; Munroe, A. M.; Hashimoto, S. J. Am. Chem. Soc. 1980, 102, 7986.
15. The remarkable regiospecificity observed has been shown to be primarily due to the alcoholic group: Finan, J. M.; Kishi, Y.; manuscript in preparation.
16. Jordaan, J. H.; Serfontein, W. J. J. Org. Chem. 1963, 28, 1395.