2-Dienylphenacyloxazolones and an intramolecular Diels-Alder approach to the A-B-C ring system of phenanthridone alkaloids

Tetrahedron

Volumn 65, Issue 43, 2009, Pages 8781-8785

  Gaenzler, Faith Corbo ^a   Azab, Mohammad E ^b   Salem, Mounir A I ^b  

^a Lisa)   (United States)

^b Ain Shams University   (Egypt)

Author keywords

Alkaloid; Diels Alder; Oxazolone; Phenanthridones; Synthesis

Indexed keywords

2 BUTADIENYLBENZOIC ACID DERIVATIVE; 2 DIENYLPHENACYCLOXAZOLONE DERIVATIVE; ALKALOID DERIVATIVE; BENZOIC ACID DERIVATIVE; OXAZOLONE; PHENANTHRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CYCLOADDITION; DIELS ALDER REACTION; HYDROLYSIS; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

ALNUS;

EID: 70349139230     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.08.066     Document Type: Article

References (38)

1. Martin S.F. The Amaryllidaceae Alkaloids. In: Brossi A. (Ed). The Alkaloids Vol. 30 (1987), Academic, New York, NY 251-376 (see p 296)
2. Mondon A., and Krohn K. Chem. Ber. 108 (1975) 445-463
3. Pettit G.R., Gaddamidi V., and Cragg G.M. J. Nat. Prod. 47 (1984) 1018-10209
4. Pettit G.R., Gaddamidi V., Cragg G.M., Herald D.L., and Sagawa Y. J. Chem. Soc., Chem. Commun. (1984) 1693-1694
5. Pettit G.R., Gaddamidi V., Herald D.L., Singh S.B., Cragg G.M., Schmidt J.M., Boettner F.E., Williams M., and Sagawa Y. J. Nat. Prod. 49 (1986) 995-1002
6. Piozzi F., Marino M.L., Fuganti C., and Di Martino A. Phytochemistry 8 (1969) 1745-1748
7. Piozzi F., Fuganti C., Mondelli R., and Ceriotti G. Tetrahedron 24 (1968) 1119-1131
8. Okamoto T., Torii Y., and Isogai Y. Chem. Pharm. Bull. 16 (1968) 1860-1864
9. Kotera K. Tetrahedron 12 (1961) 248-261
10. Ueda N., Tokuyama T., and Sakan T. Bull. Chem. Soc. Jpn. 39 (1966) 2012-2014
11. Umezawa B., Hoshino O., Sawaki S., Sato S., and Numao N. J. Org. Chem. 42 (1977) 4272-4275
12. Higashiyama H., Honda T., Otamasu H., and Kametani T. Planta Med. 48 (1983) 268-271
13. Cook J.W., and Loudon J.D. In: Manske R.H.F., and Holmes H.L. (Eds). The Alkaloids Vol. II (1952), Academic, New York, NY 331-352 (see pp 336-343)
14. Ewins A.J. J. Chem. Soc. 97 (1910) 2406-2409
15. [. Chem. Abstr. 114 (1991) 161113b ]
16. Ghosal S., Lochan R., Ashutosh K.Y., and Srivastava R.S. Phytochemistry 24 (1985) 1825-1828
17. Ghosal S., Singh S., Kumar Y., and Srivastava R.S. Phytochemistry 28 (1989) 611-613
18. Ghosal S., Datta K., Singh S.K., and Kumar Y. J. Chem. Res., Synop. (1990) 334-335
19. Hartwell J.L. Lloydia 30 (1967) 379-436
20. ElAshry S.H., and ElNemr A. Phenanthridone Alkaloids in Synthesis of Naturally Occurring Nitrogen Heterocycles from Carbohydrates (2005), Wiley, Hoboken, NJ pp 402-418; Also see:
21. Danishefsky S., and Lee J.Y. J. Am. Chem. Soc. 111 (1989) 4829-4837
22. Hudlicky T., Tian X., and Königsberger K. J. Am. Chem. Soc. 117 (1995) 3643-3644
23. Hudlicky T., Tian X., Königsberger K., Maurya R., Rouden J., and Fan B. J. Am. Chem. Soc. 118 (1996) 10752-10765
24. Trost B.M., and Pulley S.R. J. Am. Chem. Soc. 117 (1995) 10143-10144
25. Morgans Jr. D.J., and Stork G. Tetrahedron Lett. (1979) 1959-1962
26. Stork G., and Morgans Jr. D.J. J. Am. Chem. Soc. 101 (1979) 7110-7111
27. Keck G.E., Boden E., and Sonnewald U. Tetrahedron Lett. 22 (1981) 2615-2618
28. Scholz K.-H., Heine H.-G., and Hartmann W. Liebigs Ann. Chem. (1977) 2027-2035
29. Scholz K.-H., Heine H.-G., and Hartmann W. Org. Synth. Coll. Vol. 7 (1989) 4-5
30. Deyrup J.A., and Gingrich H.L. Tetrahedron Lett. (1977) 3115-3118
31. Fearnley S.P., and Market E. Chem. Commun. (2002) 438-439
32. Gaenzler F.C., and Smith M.B. Synlett (2007) 1299-1301
33. Brown C., and Sargent M. J. Chem. Soc. C (1969) 1818-1820
34. Low C. Synlett (1991) 123-124
35. Dhar M., and Bhattacharjya A. Indian J. Chem., Sect. B 40B (2001) 1140-1143
36. Bastian J.M., Ebnoether A., Jucker E., Rissi E., Stoll A.P., Sandoz A.-G., and Basel S. Helv. Chim. Acta 49 (1966) 214-234
37. Padwa A., Kulkami Y.S., and Terry L.W. J. Org. Chem. 55 (1990) 2478-2486
38. Kumar V., Chimni S.S., and Kumar S. Tetrahedron Lett. 45 (2004) 3409-3412