Application of ene-like reactions of aldehydes with vinyl ethers: Facile assembly of benzazocenone intermediates for mitomycinoids

Tetrahedron Letters

Volumn 38, Issue 25, 1997, Pages 4355-4358

  Ciufolini, Marco A ^a   Chen, Mingying ^a   Lovett, Dennis P ^a   Deaton, Melissa V ^a  

^a RICE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZAZOCINE DERIVATIVE; MITOMYCIN DERIVATIVE;

ARTICLE; DIASTEREOISOMER; DRUG SYNTHESIS; ISOMER; STEREOCHEMISTRY;

EID: 0030900077     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00933-7     Document Type: Article

References (21)

1. Fellow of the Alfred P. Sloan Foundation.
2. Reviews: (a) Kishi, Y. J. Nat. Prod. 1979, 42, 549;
3. (b) Remers, W. A.; Dorr, R. T., in: Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; John Wiley & Sons: New York, NY, 1988; vol. 6, ch. 1. Recent syntheses:
4. (c) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1987, 109, 7881;
5. (d) Schkeryantz, J. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 4722.
6. Ref. 2a-b as well as: (a) Fukuyama, T.; Xu, L. J. Am. Chem. Soc. 1992, 114, 383;
7. (b) Katoh, T.; Itoh, E.; Yoshino, T.; Terashima, S Tetrahedron Lett. 1996, 37, 3471;
8. (c) Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron Lett. 1996, 37, 3475;
9. (d) Katoh, T.; Yoshino, T.; Nagata, Y.; Nakatani, S.; Terashima, S. Tetrahedron Lett. 1996, 37, 3479.
10. (a) Martin, S. F.; Wagman, A. S. Tetrahedron Lett. 1995, 36, 1169;
11. (b) Martin, S. F.; Chen, H. J.; Courtney, A. K.; Liao, Y. S.; Patzel, M.; Ramser, M. N.; Wagman, A. S. Tetrahedron 1996, 52, 7251.
12. Deaton, M. V.; Ciufolini, M. A. Tetrahedron Lett. 1993, 34, 2409.
13. Ciufolini, M. A., in: Advances in Heterocyclic Natural Product Synthesis ; Pearson, W. H., Ed.; JAI Press: Greenwich, CT, 1996, vol. 3, ch. 1.
14. Ciufolini, M. A.; Deaton, M. V.; Zhu, S.; Chen, M. Tetrahedron 1997, 53, In Press.
15. a. Made from 2-(2-aminophenyl)-ethanol (Aldrich) by (i) diazotization/azidation; (ii) PCC oxidation (≈40%).
16. Cf.: b. Ardakani, M. A.; Smalley, R. K.; Smith, R. H. J. Chem. Soc., Perkin Trans. I 1986, 4139.
17. All calculations (MM+ force field) were carried out with the Hyperchem 4.0® package, by Hypercube, Inc..
18. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
19. We thank Drs. Lawrence Alemany and William Wilson for invaluable assistance with these measurements.
20. Related eliminations tend to occur away from heteroatoms, e.g.: Danishefsky, S.; Berman, E. M.; Ciufolini, M.; Etheredge, S. J.; Segmuller, B. E. J. Am. Chem. Soc. 1985, 107, 3891.
21. 3) 7.45-7.20 (m, 5H), 5.02 (dt, 1H, J = 9.6, 5.3), 3.81 (d, 1H, J = 16.7), 3.58 (d, 1H, J = 16.7), 2.82 (dt, 1H, J = 13.8, 3.5), 2.55 (dd, 1H, J = 13.8, 9.8), 1.80 (s, 3H).