Total synthesis of (-)-solanapyrone A via enzymatic Diels-Alder reaction of prosolanapyrone

Journal of Organic Chemistry

Volumn 63, Issue 24, 1998, Pages 8748-8756

  Oikawa, Hideaki ^a   Kobayashi, Tomonori ^a   Katayama, Kinya ^a   Suzuki, Yuichi ^a   Ichihara, Akitami ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PLANT TOXIN; PYRONE DERIVATIVE; SOLANAPYRONE A; SYNTHETASE; UNCLASSIFIED DRUG;

ALTERNARIA; ARTICLE; ENANTIOMER; ENZYME KINETICS; REACTION ANALYSIS; SYNTHESIS;

EID: 0031765407     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980743r     Document Type: Article

References (28)

1. Ichihara, A.; Tazaki, H.; Sakamura, S. Tetrahedron Lett. 1983, 24, 5373-5376.
2. Ichihara, A.; Miki, M.; Sakamura, S. Tetrahedron Lett. 1985, 26, 2453-2454.
3. Oikawa, H.; Yokota, T.; Ichihara, A.; Sakamura, S. J. Chem. Soc., Chem. Commun. 1989, 1284-1285.
4. Alam, S. S.; Bilton, J. M.; Slawin, M. Z.; Williams, D. J.; Sheppard, R. N.; Strange, R. M. Phytochemistry 1989, 28, 2627-2630.
5. Oikawa, H.; Suzuki, Y.; Naya, A.; Katayama, K.; Ichihara, A. J. Am. Chem. Soc. 1994, 116, 3605-3606.
6. Oikawa, H.; Yokota, T.; Abe, T.; Ichihara, A.; Sakamura, S.; Yoshizawa, Y.; Vederas, J. C. J. Chem. Soc., Chem. Commun. 1989, 1282-1284.
7. Oikawa, H.; Katayama, K.; Suzuki, Y.; Ichihara, A. J. Chem. Soc., Chem. Commun. 1995, 1321-1322. Ichihara, A.; Oikawa, H. Dynamic Aspects of Natural Products Chemistry: Molecular Biological Approaches; Ogura, K., Sankawa, U., Eds.; Koudannsha Scientific: Tokyo, 1997; pp 119-144.
8. Oikawa, H.; Katayama, K.; Suzuki, Y.; Ichihara, A. J. Chem. Soc., Chem. Commun. 1995, 1321-1322. Ichihara, A.; Oikawa, H. Dynamic Aspects of Natural Products Chemistry: Molecular Biological Approaches; Ogura, K., Sankawa, U., Eds.; Koudannsha Scientific: Tokyo, 1997; pp 119-144.
9. Katayama, K.; Kobayashi, T.; Oikawa, H.; Honma, M.; Ichihara, A. Biochim. Biophys. Acta 1998, 1384, 387-395.
10. Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis; VCH Publishers: New York, 1995.
11. Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071-1140.
12. Ichihara, A.; Miki, M.; Tazaki, H.; Sakamura, S. Tetrahedron Lett. 1987, 28, 1175-1178.
13. Cervello, J.; Marquet, J.; Mañas, M. M. Tetrahedron 1990, 46, 2035-2046.
14. The pyrone 13 was prepared by condensation of formaldehyde, thiophenol, and commercially available pyrone 16, see: Mañas, M. M.; Pleixats, R. Synthesis 1984, 430-431.
15. Poulton, G. A.; Cyr, T. D. Can. J. Chem. 1982, 60, 2821-2829.
16. Comins, D. L. Synlett 1992, 615-625.
17. Due to the low solubility of the pyrones, we could not test other solvents.
18. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156. For preparation of Dess-Martin periodinane, see: Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
19. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156. For preparation of Dess-Martin periodinane, see: Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
20. Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408-7410.
21. Evans, D. A.; Black, W. C. J. Am. Chem. Soc. 1993, 115, 4497-4513
22. 19 the model reaction using decanal was employed in dioxane/THF (6:1) in the presence of pyrone 19a, we could improve an isomer ratio of the vinyl iodide (E/Z = 19:1) but none of 19a was recovered. We found that iodine liberated during the reaction caused decomposition of the pyrone moiety in removal of solvent. However, we could not identify other factors for the decomposition.
23. Goure, W. F.; Wright, M. E.; Davis, P. D.; Labadie, S. S.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 6417-6422.
24. Raimondi, L.; Brown, F. K.; Gonzalez, J.; Houk, K. N. J. Am. Chem. Soc. 1992, 114, 4796-4804.
25. Breslow, R. Acc. Chem. Res. 1991, 24, 159-164.
26. Ruiz-López, M. F.; Assfeld, X.; García, J. I.; Mayoral, J. A.; Salvatella, L. J. Am. Chem. Soc. 1993, 115, 8780-8787.
27. Ichihara, A.; Oikawa, H. Curr. Org. Chem. 1998, 2, 365-394.
28. Suzuki, E. Synthesis 1978, 144-146.