Studies towards the synthesis of coprinolone, Δ6- coprinolone, and radulone A via an anionic electrocyclization cascade

Synlett

Volumn , Issue 14, 2008, Pages 2087-2088

  Lawrence, Andrew L ^a   Lee, Victor ^a   Adlington, Robert M ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

Cascade reactions; Electrocyclic reactions; Protoilludane; Sesquiterpenes; Trienone

Indexed keywords

ALCOHOL; CARBON; COPRINOLONE; CYCLOHEXANE; CYCLOPENTANE; DELTA 6 COPRINOLONE; NATURAL PRODUCT; RADULONE A; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DIELS ALDER REACTION; DRUG PURIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; SUZUKI REACTION;

EID: 51149103072     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078569     Document Type: Article

References (14)

1. (a) Starrat, A. N.; Ward, E. W. B.; Stothers, J. B. Can. J. Chem. 1989, 67, 417.
2. (b) Starrat, A. N.; Ward, E. W. B.; Stothers, J. B. J. Chem. Soc., Chem. Commun. 1988, 9, 590.
3. Fabian, K.; Lorenzen, K.; Anke, T.; Johansson, M.; Sterner, O. Z. Naturforsch., C: Biosci. 1998, 53, 939.
4. Abraham, W. R. Curr. Med. Chem. 2001, 8, 583.
5. Lawrence, A. L.; Wegner, H. A.; Jacobsen, M. F.; Adlington, R. M.; Baldwin, J. E. Tetrahedron Lett. 2006, 47, 8717.
6. Travis, B. R.; Narayan, R. S.; Borhan, B. J. Am. Chem. Soc. 2001, 124, 3824.
7. (a) Peelen, T. J.; Chi, Y.; English, E. P.; Gellman, S. H. Org. Lett. 2004, 6, 4411.
8. (b) It should be noted that addition of the diester to the basic solution had to be slow (≥ 4 h) otherwise low yields of impure product were obtained.
9. (a) Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1992, 42, 6299.
10. (b) Comins, D. L.; Dehghani, A.; Foti, C. J.; Joseph, S. P. Org. Synth. 1997, 74, 77.
11. General procedure for Pd-catalyzed Negishi coupling taken from: Milne, J. E.; Buchwald, S. L. J. Am. Chem. Soc. 2004, 126, 13028.
12. Luche, J. L.; Petrier, C.; Einhorn, J. Tetrahedron Lett. 1985, 26, 1445.
13. Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019.
14. Snider, B. B.; Harvey, T. C. J. Org. Chem. 1994, 59, 504.