Divergent approach to the polymaxenolide and pinnaic acid cores

Tetrahedron

Volumn 67, Issue 27-28, 2011, Pages 4988-4994

  Ferrari, Frank D ^a   Ledgard, Andrew J ^b   Marquez, Rodolfo ^a  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

Pinnaic acid; Polymaxenolide; Spirocyclic piperidines; Spirocyclic pyrans

Indexed keywords

1 (FURAN 2 YL)CYCLOBUTANOL; 1 (FURAN 2 YL)CYCLOHEPTANOL; 1 (FURAN 2 YL)CYCLOHEXANOL; 1 (FURAN 2 YL)CYCLOOCTANOL; 1 (FURAN 2 YL)CYCLOPENTANAMINE; 2 (1 AZIDOCYCLOPENTYL)FURAN; 2 ALLYL 1 OXASPIRO[5.5]UNDEC 3 EN 5 ONE; 2 ALLYL 1 OXASPIRO[5.6]DODEC 3 EN 5 ONE; 2 ALLYL 1 OXASPIRO[5.7]DODEC 3 EN 5 ONE; 6 ALLYL 5 OXASPIRO[3.5]NON 7 EN 9 ON; 7 ALLYL 6 AZASPIRO[4.5]DECAN 10 ONE; 7 ALLYL 6 AZASPIRO[4.5]DECANE; 7 ALLYL 6 OXASPIRO[4.5]DECAN 10 ONE; 7 ALLYL 6 OXASPIRO[4.5]DECANE; 7 ALLYL 6 TOSYLAZASPIRO[4.5]DEC 8 EN 10 ONE; 7 HYDROXY 6 TOSYL 6 AZASPIRO[4.5]DEC 8 EN 10 ONE; ETHYL 2 METHYL 4 (6 AZASPIRO[4.5]DECAN 7 YL)BUT 2 ENOATE; ETHYL 2 METHYL 4 (6 OXASPIRO[4.5]DECAN 7 YL)BUT 2 ENOATE; FURAN DERIVATIVE; N (1 FURAN 2 YL)CYCLOPENTYL 4 TOLUENESULFONAMIDE; PINNAIC ACID; PIPERIDINE DERIVATIVE; POLYMAXENOLIDE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CHEMICAL REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 79958724541     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.04.047     Document Type: Article

References (20)

1. Chou, T.; Kuramoto, M.; Otani, Y.; Shikano, M.; Yazawa, K.; Uemura, D. Tetrahedron Lett. 1996, 37, 3871.
2. Kuramoto, M.; Tong, C.; Yamada, K.; Chiba, T.; Hayashi, Y.; Uemura, D. Tetrahedron Lett. 1996, 37, 3867.
3. (a) Kamel, H. N.; Fronczek, F. R.; Fischer, N. H.; Slattery, M. Tetrahedron Lett. 2004, 45, 1995;
4. (b) Kamel, H. N.; Ding, Y.; Li, X.-C.; Ferreira, D.; Fronczek, F. R.; Slattery, M. J. Nat. Prod. 2009, 72, 900.
5. Kirk, H.; Choi, Y. H.; Kim, H. K.; Verpoorte, R.; Meijden, E. New Phytol. 2005, 167, 613.
6. For an excellent review on the synthetic chemistry of halichlorine and the pinnaic acids please see: Clive, D. L. J.; Yu, M.; Wang, J.; Yeh, V. S. C.; Kang, S. Chem. Rev. 2005, 105, 4483.
7. For more recent approaches: (a) Andrade, R. B.; Martin, S. F. Org. Lett. 2005, 7, 5733;
8. (b) Wu, H.; Zhang, H.; Zhao, G. Tetrahedron 2007, 63, 6454;
9. (c) Yang, S. H.; Caprio, V. Synlett 2007, 1219;
10. (d) Xu, S.; Arimoto, H.; Uemura, D. Angew. Chem., Int. Ed. 2007, 46, 5746;
11. (e) Hurley, P. B.; Drake, G. R. J. Org. Chem. 2008, 73, 4131;
12. (f) Keck, G. E.; Heumann, S. A. Org. Lett. 2008, 10, 4783;
13. (g) Yang, S. H.; Clark, G. R.; Caprio, V. Org. Biomol. Chem. 2009, 7, 2981.
14. Hobson, S. J.; Marquez, R. Org. Biomol. Chem. 2006, 4, 3808.
15. Romero, J. A. C.; Tabacco, S. A.; Woerpel, K. A. J. Am. Chem. Soc. 2000, 122, 168.
16. For some recent examples of the aza-Achmatowicz rearrangement in synthesis: (a) Cassidy, M. P.; Padwa, A. Org. Lett. 2004, 6, 4029;
17. (b) Leverett, C. A.; Cassidy, M. P.; Padwa, A. J. Org. Chem. 2006, 71, 8591.
18. Koulocheri, S. D.; Haroutounian, S. A.; Apostolopoulos, C. D.; Chada, R. K.; Couladouros, E. A. Eur. J. Org. Chem. 1999, 1449.
19. Mahoney, W. S.; Brestensky, D. M.; Stryker, J. M. J. Am. Chem. Soc. 1988, 110, 291.
20. Hopman, J. C. P.; van den Berg, E.; Ollero Ollero, L.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1995, 36, 4315.