Heterocyclisation via 1,3-Cyclic Sulfates. Asymmetric Synthesis of (+)-Sedridine

Synlett

Volumn 1997, Issue 1, 1997, Pages 22-24

  Littler, Benjamin J ^a   Gallagher, Timothy ^a   Boddy, Ian K ^b   Riordan, Peter D ^b  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b AgrEvo UK Limited   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001776870     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-699     Document Type: Article

References (19)

1. Lohray, B. B. Synthesis 1992, 1035.
2. Kalanter, T. H.; Sharpless, K. B. Acta Chem. Scand. 1993, 47, 307; Beauchamp, T. J.; Powers, J. P.; Rychnovsky, S. D. J. Am. Chem. Soc. 1995, 117, 12873.
3. Kalanter, T. H.; Sharpless, K. B. Acta Chem. Scand. 1993, 47, 307; Beauchamp, T. J.; Powers, J. P.; Rychnovsky, S. D. J. Am. Chem. Soc. 1995, 117, 12873.
4. For an example of a cyclisation reaction of a 1,3-cyclic sulfate leading to an oxetane, see Denmark, S. E. J. Org. Chem. 1981, 46, 3144.
5. Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538.
6. 4) and concentrated. Filtration through a pad of silica gel (eluting with EtOAc-hexane, 1:1) gave N-tosyl sedridine (214 mg, 99 %) as a colourless oil which crystallised on standing.
7. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
8. Isolation of (+)-sedridine (9): (a) Beyerman, H. C.; Muller, Y. M. F. Rec. Trav. Chim. 1955, 74, 1568. (b) Schöpf, C.; Unger, R. Experimentia 1956, 12, 19. Assignment of absolute configuration of (+)-sedridine: (c) Butruille, D.; Fodor, G.; Saunderson Huber, C.; Letourneau, F. Tetrahedron 1971, 27, 2055 and references therein. Asymmetric syntheses of (+)-sedridine (other than methods involving resolution): (d) Murahashi, S.; Imada, Y.; Kohno, M.; Kawakami, T. Synlett, 1993, 395. (e) Louis, C.; Hootelé, C. Tetrahedron: Asymmetry 1995, 6, 2149.
9. Isolation of (+)-sedridine (9): (a) Beyerman, H. C.; Muller, Y. M. F. Rec. Trav. Chim. 1955, 74, 1568. (b) Schöpf, C.; Unger, R. Experimentia 1956, 12, 19. Assignment of absolute configuration of (+)-sedridine: (c) Butruille, D.; Fodor, G.; Saunderson Huber, C.; Letourneau, F. Tetrahedron 1971, 27, 2055 and references therein. Asymmetric syntheses of (+)-sedridine (other than methods involving resolution): (d) Murahashi, S.; Imada, Y.; Kohno, M.; Kawakami, T. Synlett, 1993, 395. (e) Louis, C.; Hootelé, C. Tetrahedron: Asymmetry 1995, 6, 2149.
10. Isolation of (+)-sedridine (9): (a) Beyerman, H. C.; Muller, Y. M. F. Rec. Trav. Chim. 1955, 74, 1568. (b) Schöpf, C.; Unger, R. Experimentia 1956, 12, 19. Assignment of absolute configuration of (+)-sedridine: (c) Butruille, D.; Fodor, G.; Saunderson Huber, C.; Letourneau, F. Tetrahedron 1971, 27, 2055 and references therein. Asymmetric syntheses of (+)-sedridine (other than methods involving resolution): (d) Murahashi, S.; Imada, Y.; Kohno, M.; Kawakami, T. Synlett, 1993, 395. (e) Louis, C.; Hootelé, C. Tetrahedron: Asymmetry 1995, 6, 2149.
11. Isolation of (+)-sedridine (9): (a) Beyerman, H. C.; Muller, Y. M. F. Rec. Trav. Chim. 1955, 74, 1568. (b) Schöpf, C.; Unger, R. Experimentia 1956, 12, 19. Assignment of absolute configuration of (+)-sedridine: (c) Butruille, D.; Fodor, G.; Saunderson Huber, C.; Letourneau, F. Tetrahedron 1971, 27, 2055 and references therein. Asymmetric syntheses of (+)-sedridine (other than methods involving resolution): (d) Murahashi, S.; Imada, Y.; Kohno, M.; Kawakami, T. Synlett, 1993, 395. (e) Louis, C.; Hootelé, C. Tetrahedron: Asymmetry 1995, 6, 2149.
12. Isolation of (+)-sedridine (9): (a) Beyerman, H. C.; Muller, Y. M. F. Rec. Trav. Chim. 1955, 74, 1568. (b) Schöpf, C.; Unger, R. Experimentia 1956, 12, 19. Assignment of absolute configuration of (+)-sedridine: (c) Butruille, D.; Fodor, G.; Saunderson Huber, C.; Letourneau, F. Tetrahedron 1971, 27, 2055 and references therein. Asymmetric syntheses of (+)-sedridine (other than methods involving resolution): (d) Murahashi, S.; Imada, Y.; Kohno, M.; Kawakami, T. Synlett, 1993, 395. (e) Louis, C.; Hootelé, C. Tetrahedron: Asymmetry 1995, 6, 2149.
13. Huckin, S. N.; Weiler, L. J. Am. Chem. Soc. 1974, 96, 1082.
14. King, S. A.; Thompson, A. S.; King, A. O.; Verhoeven, T. R. J. Org. Chem. 1992, 57, 6689.
15. 1H NMR using the Mosher ester derivative, with (±)-(5) being used as a standard.
16. 3H (Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560). Anti-diol (10) has been converted to (-)-allosedridine using the same procedures as illustrated in Scheme 2. (Equation Presented)
17. 3H (Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560). Anti-diol (10) has been converted to (-)-allosedridine using the same procedures as illustrated in Scheme 2. (Equation Presented)
18. 7e}.
19. Fletcher, D. A.; McMeeking, R. F.; Parkin, D. J. J. Chem. Inf. Comput. Sci. 1996, 36, 746.