A Convenient Synthesis of A-Ring-Functionalized Podolactones. Revision of the Structure of Wentilactone B

Organic Letters

Volumn 4, Issue 8, 2002, Pages 1379-1382

  Barrero, Alejandro F ^a   Herrador, María M ^a   Quílez Del Moral, José F ^a   Valdivia, Mónica V ^a  

^a UNIVERSITY OF GRANADA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FUSED HETEROCYCLIC RINGS; LACTONE; TERPENE; WENTILACTONE B;

ARTICLE; CHEMISTRY; CONFORMATION; CYCLIZATION; MEDICINAL PLANT; SYNTHESIS;

CYCLIZATION; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; INDICATORS AND REAGENTS; LACTONES; MOLECULAR CONFORMATION; PLANTS, MEDICINAL; TERPENES;

EID: 0037129423     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0257070     Document Type: Article

References (28)

1. In Dictionary of Terpenoids; Connolly, J. D., Hill, R. A. Eds.; Chapman & Hall: London, U.K., 1991; Vol. 2, pp 853-857.
2. (a) Andersen, N. R.; Rasmunsen, P. R. Tetrahedron Lett. 1984.
3. (b) Dorner, J. W.; Cole, R. J.; Springer, J. P.; Cox, R. H.; Cutler, H.; Wicklow, D. T. Phytochemistry 1980, 19, 1157.
4. (c) Ellestad, G. A.; Evans, R. H.; Kunstmann, M. P.; Lancaster, J. E.; Morton, G. O. J. Am. Chem. Soc. 1970, 92, 5483.
5. (a) Hembree, J. A.; Chang, C.; McLaughlin, J. L.; Cassady, J. M.; Watts, D. J.; Wenkert, E.; Fonseca, S. F.; De Paiva Campello, J. Phytochemistry 1979, 18, 1691.
6. (b) Singh, P.; Russell, G. B.; Hayashi, Y.; Gallagher, R. T.; Fredericksen, S. Entomol. Exp. Appl. 1979, 25, 121.
7. (c) Zhang, M.; Ying, B. P.; Kubo, I. J. Nat. Prod. 1992, 55, 1057.
8. (d) Macías, F. A.; Simonet, A. M.; Pacheco, P. C.; Barrero, A. P.; Cabrera, E.; Jiménez-González, D. J. Agric. Food Chem. 2000, 48, 3003.
9. (e) Hosoe, T.; Nozawa, K.; Lumley, T. C.; Currah, R. S.; Fukushima, K.; Takizawa, K.; Miyaji, M.; Kawai, K. Chem. Pharm. Bull. 1999, 47, 1591.
10. Ichikawa, K.; Ikunaka, M.; Kojima, N.; Nishida, H.; Yoshikawa, N. European Patent 0 933 273 A1, 1999.
11. Barrero, A. F.; Quílez del Moral, J. F.; Cuerva, J. M.; Cabrera, E.; Jiménez-González, D. Tetrahedron Lett. 2000, 41, 5203.
12. To our knowledge, only one A-ring-functionalized podolactone, (±)3β-hydroxynagilactone F, has been previously synthesized. This synthesis was reported by de Groot et al. in less than 0.1 % yield: Reuvers, J. T. A.; de Groot, A. J. Org. Chem. 1986, 51, 4594.
13. (a) Bäckvall, J. E.; Byström, S. E.; Nordberg, R. E. J. Org. Chem. 1984, 49, 4619.
14. (b) Bäckvall, J. E. In Metal-Catalyzed Cross-Coupling Reactions; Stang, P.. Diederich, F., Eds.; Wiley-VCH: Weinham, 1998; pp 339-385.
15. Corey, E. J.; Kim, C. U.; Takeda, M. Tetrahedron Lett. 1972, 13, 5203.
16. Oxidative radical cyclization of polyenes with Mn(III) and Cu(II) has been widely used in the synthesis of policyclic compounds. For recent examples see: (a) Yang, D.; Xu, M. Org. Lett. 2001, 3, 1785 and references therein. For a review, see: (b) Snider, B. B. Chem. Rev. 1996, 96, 339.
17. Oxidative radical cyclization of polyenes with Mn(III) and Cu(II) has been widely used in the synthesis of policyclic compounds. For recent examples see: (a) Yang, D.; Xu, M. Org. Lett. 2001, 3, 1785 and references therein. For a review, see: (b) Snider, B. B. Chem. Rev. 1996, 96, 339.
18. The cyclization of 10 to give 11 in 58% yield has been previously reported by Zoretic et al. in their synthesis of d,l-norlabdane oxide: Zoretic, P. A.; Haiquan, F.; Ribeiro, A. A. J. Org. Chem. 1998, 63, 4779.
19. Radical cyclization has been described to proceed with total stereoselectivity. Furthermore, in works published by us and others, double bonds with Z configuration have been reported not to react with free radicals: (a) Barrero, A. F.; Cuerva, J. M.; Herrador, M. M.; Valdivia, M. V. J. Org. Chem. 2001, 66, 4074. (b) Julia, M. Acc. Chem. Res. 1971, 4, 386.
20. Radical cyclization has been described to proceed with total stereoselectivity. Furthermore, in works published by us and others, double bonds with Z configuration have been reported not to react with free radicals: (a) Barrero, A. F.; Cuerva, J. M.; Herrador, M. M.; Valdivia, M. V. J. Org. Chem. 2001, 66, 4074. (b) Julia, M. Acc. Chem. Res. 1971, 4, 386.
21. In Handbook of Reagents for Organic Synthesis. Reagents, Auxiliaries, and Catalysts for C-C Bond Formation; Coates, R. M., Denmark, S. E., Eds.; John Wiley & Sons Ltd: Chichester, 1999; pp 180-184.
22. (a) Although few examples of intramolecular nucleophilic attack of a carboxylate to conjugate dienes leading to a monolactone have been described (Jonasson, C.; Rönn, M.; Bäckvall, J. E. J. Org. Chem. 2000, 67, 2122), this bislactonization process has been successfully applied only once before by our group in the synthesis of oidiolacone C: Barrero, A. F.; Arseniyadis, S.; Quílez del Moral, J. F.; Herrador, M. M.; Valdivia, M.; Jiménez, D. J. Org. Chem. 2002, in press. (b) Bäckvall, J. E.; Granberg, K. L.; Andersson, P. G.; Gatti, R.; Gogoll, A. J. Org. Chem. 1993, 58, 5445.
23. (a) Although few examples of intramolecular nucleophilic attack of a carboxylate to conjugate dienes leading to a monolactone have been described (Jonasson, C.; Rönn, M.; Bäckvall, J. E. J. Org. Chem. 2000, 67, 2122), this bislactonization process has been successfully applied only once before by our group in the synthesis of oidiolacone C: Barrero, A. F.; Arseniyadis, S.; Quílez del Moral, J. F.; Herrador, M. M.; Valdivia, M.; Jiménez, D. J. Org. Chem. 2002, in press. (b) Bäckvall, J. E.; Granberg, K. L.; Andersson, P. G.; Gatti, R.; Gogoll, A. J. Org. Chem. 1993, 58, 5445.
24. (a) Although few examples of intramolecular nucleophilic attack of a carboxylate to conjugate dienes leading to a monolactone have been described (Jonasson, C.; Rönn, M.; Bäckvall, J. E. J. Org. Chem. 2000, 67, 2122), this bislactonization process has been successfully applied only once before by our group in the synthesis of oidiolacone C: Barrero, A. F.; Arseniyadis, S.; Quílez del Moral, J. F.; Herrador, M. M.; Valdivia, M.; Jiménez, D. J. Org. Chem. 2002, in press. (b) Bäckvall, J. E.; Granberg, K. L.; Andersson, P. G.; Gatti, R.; Gogoll, A. J. Org. Chem. 1993, 58, 5445.
25. Kubo, I.; Himejina, M.; Ying, B. P. Phytochemistry 1991, 30, 1469.
26. (-)-8-Phenylmenthol has been reported both to induce a good diastereomer ratio and to proceed with high yield in Mn(III)-based asymmetric radical cyclization of related β-keto esters; see: (a) Yang, D.; Ye, X.-Y.; Xu. M. J. Org. Chem. 2000, 65, 2208. (b) Zhang, Q.-W.; Mohan, R. M.; Cook, L.; Kazanis, S.; Peisach, D.; Foxman, B. M.; Snider, B. B.. J. Org. Chem. 1993, 58, 7640. (c) Zoretic, P. A.; Weng, X.; Biggers, M. S.; Caspar, M. L.; Davis, D. G. Tetrahedron Lett. 1992, 33, 2637.
27. (-)-8-Phenylmenthol has been reported both to induce a good diastereomer ratio and to proceed with high yield in Mn(III)-based asymmetric radical cyclization of related β-keto esters; see: (a) Yang, D.; Ye, X.-Y.; Xu. M. J. Org. Chem. 2000, 65, 2208. (b) Zhang, Q.-W.; Mohan, R. M.; Cook, L.; Kazanis, S.; Peisach, D.; Foxman, B. M.; Snider, B. B.. J. Org. Chem. 1993, 58, 7640. (c) Zoretic, P. A.; Weng, X.; Biggers, M. S.; Caspar, M. L.; Davis, D. G. Tetrahedron Lett. 1992, 33, 2637.
28. (-)-8-Phenylmenthol has been reported both to induce a good diastereomer ratio and to proceed with high yield in Mn(III)-based asymmetric radical cyclization of related β-keto esters; see: (a) Yang, D.; Ye, X.-Y.; Xu. M. J. Org. Chem. 2000, 65, 2208. (b) Zhang, Q.-W.; Mohan, R. M.; Cook, L.; Kazanis, S.; Peisach, D.; Foxman, B. M.; Snider, B. B.. J. Org. Chem. 1993, 58, 7640. (c) Zoretic, P. A.; Weng, X.; Biggers, M. S.; Caspar, M. L.; Davis, D. G. Tetrahedron Lett. 1992, 33, 2637.