Synthesis of highly functionalised enantiopure bicyclo[3.2.1]-octane systems from carvone

Molecules

Volumn 9, Issue 5, 2004, Pages 287-299

  Abad, Antonio ^a   Agulló, Consuelo ^a   Cuñat, Ana C ^a   De Alfonso, Ignacio ^a   Navarro, Ismael ^a   Vera, Noelia ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

5 vinyl 1,3 cyclohexadiene; Bicyclo 3.2.1 octane; Carvone; Cyclopropane cleavage; Diels Alder reaction; Samarium diiodide; Tricyclo 3.2.1.0 2.7 octane

Indexed keywords

4 (TERT BUTYLDIMETHYLSILANYLOXY) 3 HYDROXY 4,7 DIMETHYLBICYCLO[3.2.1]OCT 2 ENE 2 CARBOXYLIC ACID METHYL ESTER; 4 (TERT BUTYLDIMETHYLSILANYLOXY) 3 HYDROXY 7 METHOXY 4,7 DIMETHYLBICYCLO[3.2.1]OCT 2 ENE 2 CARBOXYLIC ACID METHYL ESTER; 4 (TERT BUTYLDIMETHYLSILANYLOXY) 3,7 DIHYDROXY 4,7 DIMETHYLBICYCLO[3.2.1]OCT 2 ENE 2 CARBOXYLIC ACID METHYL ESTER; 4 (TERT BUTYLDIMETHYLSILANYLOXY) 7 CHLORO 3 HYDROXY 4,7 DIMETHYLBICYCLO[3.2.1]OCT 2 ENE 2 CARBOXYLIC ACID METHYL ESTER; 5 VINYL 1,3 CYCLOHEXADIENE; 7 BENZYLOXY 4 (TERT BUTYLDIMETHYLSILANYLOXY) 3 HYDROXY 4,7 DIMETHYLBICYCLO[3.2.1]OCT 2 ENE 2 CARBOXYLIC ACID METHYL ESTER; ALKENE DERIVATIVE; BICYCLO COMPOUND; BICYCLO[3.2.1]OCTANE; CARVONE; CYCLOPROPANE; OCTANE; TERPENE; TRICYCLO[3.2.1]OCTANE; UNCLASSIFIED DRUG;

ARTICLE; DIELS ALDER REACTION; DRUG SYNTHESIS; RING OPENING;

EID: 3242883461     PISSN: 14203049     EISSN: None     Source Type: Journal    
DOI: 10.3390/90500287     Document Type: Article

References (23)

1. (a) Connolly, J. D.; Hill R. A. In Dictionary of Terpenoids, 1st Ed; Chapman and Hall: London, 1991; Vol. 2, pp. 906-970.
2. (b) Hanson, J. R. Nat. Prod. Rep. 2002, 19, 650.
3. (c) Fraga, B. M. Nat. Prod. Rep. 2002, 19, 125, and previous reviews in this series.
4. Filippini, M. H.; Rodriguez, J. Chem. Rev. 1999, 99, 27-76.
5. For recent examples, see: Magnus, P.; Rainey, T.; Lynch, V. Tetrahedron Lett. 2003, 44, 2459-2461.
6. For recent examples, see: Meijere, A.; Hadjirapoglou, L.; Noltemeyer, M.; Gutke, H-J.; Klein, I.; Spitzner, D. Eur. J. Org. Chem. 1998, 441-451 and references cited therein.
7. This work forms part of our research program directed towards the synthesis of trachylobane-beyerane- and atisane-type terpenoids, see: Abad, A.; Agulló, C.; Cuñat, A. C.; Navarro, I.; M. Carmen Ramírez de Arellano, Synlett, 2001, 3, 349-352.
8. Ciganek, E.: The intramolecular Diels-Alder reaction; Organic Reactions; John Wiley: New York, 1984; Vol 32, p. 165.
9. Stephanie, M. Ng.; Beaudry, C. M.; Trauner, D. Org. Lett. 5, 2003, 1701-1704.
10. Abad, A.; Agulló, C.; Cuñat, A. C.; García, A. B. Tetrahedron, 2003, 59, 9523-9536.
11. Ho, T.L. Ed.; Enantioselective Synthesis: Natural Products from Chiral Terpenes; John Wiley & Sons: New York, 1992.
12. Llera, J, M.; Fraser-Reid, B. J. Org. Chem.1989, 54, 5544-5548.
13. The carbobicyclic ring system formed in this Diels-Alder reaction constitutes the characteristic substructural fragment of some natural compounds endowed with significant biological activity. See, for example: (a) Fraga, B. M. Phytochem. Analysis, 1994, 5, 49-56;
14. (b) Block, S.; Stevigny, C.; De Pauw-Gillet, M. C.; de Hoffmann, E.; Llabres, G.; Adjakidje, V.; Quetin-Leclercq, J. Planta Med. 2002, 68, 647-964.
15. For examples of Diels-Alder reactions of 1,3,10-undecatrienes, see: Brocksom, T. J.; Maria, J.; Ferreira, L.; Brocksom, U. J. Braz. Chem. Soc. 2001, 12, 597-622.
16. Molander, G., Alonso-Alija C., Tetrahedron, 1997, 53, 8067-8084.
17. (a) Miller, J. A.; Ullah, G. M.; Welsh, G. M.; Mallon, P. Tetrahedron Lett. 2001, 42, 2729-2731.
18. (b) Snider, B.; Buckman, B. O. J. Org. Chem. 1992, 57, 4883-4888, and referenced cited therein.
19. (a) Meltzer, P. C.; Zhengming, P. B,; Yong, C. Y. F.; Madras, B. K. Bioorg. Med. Chem. Lett. 1999, 9, 857-862.
20. (b) Meltzer, P. C.; Blundell, P.; Huang, H.; Liu, S.; Yong, Y. F.; Madras, B. K. Bioorg. Med. Chem., 2000, 8, 581-590.
21. (c) Meltzer, P. C.; Blundell, P.; Yong, Y. F.; Chen, Z.; George, C.; Gonzalez, M. D.; Madras, B K. J. Med. Chem. 2000, 43, 2982-2991.
22. (d) Madras, B. K.; Meltzer, P. C. Brit. UK Pat., Application: GB 2002-4596 (2003).
23. Weinges, K.; Schwarz, G. Liebigs Ann. Chem. 1993, 7, 811-814.