Synthesis of fused oxabicyclic systems by metal-catalyzed intramolecular addition of 1,3-cycloalkyldiones to alkynes

Organic Letters

Volumn 5, Issue 11, 2003, Pages 1975-1977

  Gulías, Moisés ^a   Rodríguez, J Ramón ^a   Castedo, Luis ^a   Mascareñas, José L ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; KETONE DERIVATIVE; METAL COMPLEX;

ADDITION REACTION; ARTICLE; CATALYSIS; COMPLEX FORMATION; ISOMERISM; ROOM TEMPERATURE; SYNTHESIS;

EID: 0141852961     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0345632     Document Type: Article

References (24)

1. For reviews, see: (a) Méndez, M.; Echavarren, A. M. Eur. J. Org. Chem. 2002, 15. (b) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813. (c) McDonald, F. E. Chem. Eur. J. 1999, 5, 3103.
2. For reviews, see: (a) Méndez, M.; Echavarren, A. M. Eur. J. Org. Chem. 2002, 15. (b) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813. (c) McDonald, F. E. Chem. Eur. J. 1999, 5, 3103.
3. For reviews, see: (a) Méndez, M.; Echavarren, A. M. Eur. J. Org. Chem. 2002, 15. (b) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813. (c) McDonald, F. E. Chem. Eur. J. 1999, 5, 3103.
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11. For an application to the preparation of bridged oxabicycles, see: (d) Iwasawa, N.; Shido, M.; Husama, H. J. Am. Chem. Soc. 2001, 123, 5814.
12. This compound was synthesized from 1,2-cyclohexanedione; see Supporting Information and: Rodríguez, J. R.; Castedo, L.; Mascareñas, J. L. Chem. Eur. J. 2002, 8, 2923.
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15. (c) McDonald, F. E.; Olson, T. C. Tetrahedron Lett. 1997, 38, 7691.
16. See Supporting Information and: Stork, G.; Danheiser, R. J. Org. Chem. 1973, 38, 1775.
17. Tungsten-catalyzed isomerization of several 4-alkyn-1-ols proceeds in a endo-selective fashion: McDonald, F. E.; Reddy, K. S.; Díaz, Y. J. Am. Chem. Soc. 2000, 122, 4304.
18. These are important frameworks for the synthesis of prostaglandin derivatives. See for instance: (a) Newton, R. F.; Wadsworth, A. H. J. Chem. Soc., Perkin Trans. 1 1982, 823. (b) Skuballa, V. Tetrahedron Lett. 1980, 21, 3261. (c) Herndon, J. W.; Matasi, J. T. Tetrahedron Lett. 1992, 33, 5725.
19. These are important frameworks for the synthesis of prostaglandin derivatives. See for instance: (a) Newton, R. F.; Wadsworth, A. H. J. Chem. Soc., Perkin Trans. 1 1982, 823. (b) Skuballa, V. Tetrahedron Lett. 1980, 21, 3261. (c) Herndon, J. W.; Matasi, J. T. Tetrahedron Lett. 1992, 33, 5725.
20. These are important frameworks for the synthesis of prostaglandin derivatives. See for instance: (a) Newton, R. F.; Wadsworth, A. H. J. Chem. Soc., Perkin Trans. 1 1982, 823. (b) Skuballa, V. Tetrahedron Lett. 1980, 21, 3261. (c) Herndon, J. W.; Matasi, J. T. Tetrahedron Lett. 1992, 33, 5725.
21. This conclusion is inferred from a qualitative MM2 analysis of the strain energy of the oxabicyclic and bridged carbobicyclic products.
22. This type of bicyclic framework forms the basic skeletons of a variety of natural products such as bisabolane-type sesquiterpenoids. See for instance: (a) Takao, K.; Tsujita, T.; Hara, M.; Tadano, K. J. Org. Chem. 2002, 67, 6693. (b) Weyerstahl, P.; Meisel, T. Liebigs. Ann. Chem. 1994, 415.
23. This type of bicyclic framework forms the basic skeletons of a variety of natural products such as bisabolane-type sesquiterpenoids. See for instance: (a) Takao, K.; Tsujita, T.; Hara, M.; Tadano, K. J. Org. Chem. 2002, 67, 6693. (b) Weyerstahl, P.; Meisel, T. Liebigs. Ann. Chem. 1994, 415.
24. For other applications of metal-catalyzed alkene-forming reactions coupled with hydrogenation, see: Louie, J.; Bielawski, C. W.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 11312.