A concise total synthesis of (±)-alantrypinone by a novel hetero-diels-alder reaction

Organic Letters

Volumn 5, Issue 18, 2003, Pages 3205-3208

  Kende, Andrew S ^a   Fan, Junfa ^a   Chen, Zecheng ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALANTRYPINONE; ANTHRANILIC ACID; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DIELS ALDER REACTION; ISOMER; SYNTHESIS;

EID: 0141856319     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol030070l     Document Type: Article

References (20)

1. Larsen, T. O.; Frydenvang, K.; Frisvad, J. C.; Christophersen, C. J. Nat. Prod. 1998, 61, 1154-1157.
2. Ariza, M. R.; Larsen, T. O.; Petersen, B. O.; Duus, J. Q.; Christophersen, C.; Barrero, A. F. J. Nat. Prod. 2001, 64, 1590-1592.
3. Takahashi, C.; Matsushita, T.; Doi, M.; Minoura, K.; Shingu, T.; Kumeda, Y.; Numata, A. J. Chem. Soc., Perkin Trans. 1 1995, 2345-2353.
4. (a) Barrow, C. J.; Sun, H. H. J. Nat. Prod. 1994, 57, 471-476.
5. (b) Cascieri, M. A.; Macleod, A. M.; Underwood, D.; Shiao, L.-L.; Ber, E.; Sadowski, S.; Yu, H.; Merchant, K. J.; Swain, C. J.; Strader, C. D.; Fong, T. M. J. Biol. Chem. 1994, 269, 6587-6591.
6. (a) Hart, D. J.; Magomedov, N. A. J. Am. Chem. Soc. 2001, 123, 5892-5899.
7. (b) Hart, D. J.; Magomedov, N. A. Tetrahedron Lett. 1999, 40, 5429-5432.
8. Pellegrini, C.; Strassler, C.; Weber, M.; Borschberg, H.-J. Tetrahedron: Asymmetry 1994, 5, 1979-1982.
9. A possible Diels-Alder approach to the synthesis of 1 is alluded to in a footnote to the full paper by Hart and Magomedov cited as ref 5 above.
10. Hernandez, F.; Buenadicha, F. L.; Avendano, C.; Sollhuber, M. Tetrahedron: Asymmetry 2001, 12, 3387-3398.
11. Mazurkiewicz, R. Monatsh. Chem. 1989, 120, 973-980.
12. (a) Snider, B. B.; Zeng, H. Org Lett. 2000, 2, 4103-4106.
13. (b) He, H.; Snider, B. B. J. Org Chem. 1999, 64, 1397-1399.
14. For a related aromatization see: Blake, K. W.; Porter, A. E. A.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1972, 2494-2497.
15. Rossitter, S. Tetrahedron Lett. 2002, 43, 4671-4673.
16. (a) Jnoff, E.; Ghosez, L. J. Am. Chem. Soc. 1999, 121, 2617-2618.
17. (b) Rivera, M.; Lamy-Schelkens, H.; Sainte, F.; Mbiya, K.; Ghosez, L. Tetrahedron Lett. 1988, 29, 4573-4576.
18. Pouilhes, A.; Langlois, Y.; Nshimyumukiza, P.; Mbiya, K.; Ghosez, L. Bull. Soc. Chim. Fr. 1993, 130 304-309.
19. Sustmann, R.; Sicking, W. Tetrahedron 1992, 48, 10293-10300.
20. For a somewhat related retroaldol epimerization in a synthesis of (±)-gelsemine see: Atarashi, S.; Choi, J.-K.; Ha, D.-C.; Hart, D. J.; Kuzmich, D.; Lee, C.-S.; Ramesh, S.; Wu, S. C. J. Am. Chem. Soc. 1997, 119, 6226-6241. We thank Prof. N. Magomedov for calling this reference to our attention.