Total Synthesis of (+)-Nostocyclamide

Synlett

Volumn 1996, Issue 12, 1996, Pages 1171-1172

  Moody, Christopher J ^a,b   Bagley, Mark C ^a  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF EXETER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002510010     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5713     Document Type: Article

References (20)

1. Pattenden, G. J. Heterocycl. Chem. 1992, 29, 607-618.
2. Michael, J. P.; Pattenden, G. Angew. Chem. Int. Ed. Engl. 1993, 32, 1-23.
3. Wipf, P. Chem. Rev. 1995, 95, 2115-2134.
4. Doyle, K. J.; Moody, C. J. Tetrahedron 1994, 50, 3761-3772.
5. Doyle, K. J.; Moody, C. J. Synthesis 1994, 1021-1022.
6. Moody, C. J.; Swann, E. J. Chem. Soc., Perkin Trans. 1 1993, 2561-2565.
7. Todorova, A. K.; Jüttner, F.; Linden, A.; Plüss, T.; von Philipsborn, W. J. Org. Chem. 1995, 60, 7891-7895.
8. Bagley, M. C.; Buck, R. T.; Hind, S. L.; Moody, C. J.; Slawin, A. M. Z. Synlett 1996, 825.
9. Wipf, P.; Miller, C. P. J. Org. Chem. 1993, 58, 3604-3606.
10. For example, see: Boden, C. D. J.; Pattenden, G.; Ye, T. Synlett 1995, 417-419.
11. Aguilar, E.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 2473-2476.
12. Aguilar, E.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 2477-2480.
13. Bredenkamp, M. W.; Holzapfel, C. W.; Snyman, R. M.; van Zyl, W. J. Synth. Commun. 1992, 22, 3029-3039.
14. The enantiomeric purity of ester 11 was determined by HPLC on a Chiralcel OD column, eluting with hexane/2-propanol (98:2) at 0.75 mL/min. The ester 11 had m.p. 118.5-119°C (Houssin, R.; Lohez, M.; Bernier, J.-L.; Hénichart, J.-P. J. Org. Chem. 1985, 50, 2787-2788; m.p. 125.5°C).
15. Compound 3 had m.p. 180.5-182°C (Bernier, J.-L.; Houssin, R.; Hénichart, J.-P. Tetrahedron 1986, 42, 2695-2702; m.p. 184°C)
16. 2O). 4.87 (1H, m), 3.91 (3H, s), 2.62 (3H, s), 2.35 (1H, m), 1.69 (3H, d, J 7.0 Hz), 1.47 (9H, s), 1.00 (3H, d, J 6.7 Hz), and 0.93 (3H, d, J 6.9 Hz).
17. 2O), 5.38 (1H, dq, J 8.5, 7.2 Hz), 5.25 (1H, dd, J 9.2, 6.2 Hz), 4.56 (2H, d, J 4.9 Hz), 3.83 (3H, s), 2.55 (3H, s), 2.44 (1H, m), 1.62 (3H, d, J 7.0 Hz), 1.39 (9H, s), 0.96 (3H, d, J 6.7 Hz), and 0.95 (3H, d, J 6.8 Hz).
18. Schmidt, U.; Stäbler, F. J. Chem. Soc., Chem. Commun. 1992, 1353-1354; Schmidt, U.; Weinbrenner, S. J. Chem. Soc., Chem. Commun. 1994, 1003-1004.
19. Schmidt, U.; Stäbler, F. J. Chem. Soc., Chem. Commun. 1992, 1353-1354; Schmidt, U.; Weinbrenner, S. J. Chem. Soc., Chem. Commun. 1994, 1003-1004.
20. 3). We thank Professor F. Jüttner for this information.