Novel carbocyle enlargement in aqueous medium

Journal of the American Chemical Society

Volumn 118, Issue 17, 1996, Pages 4216-4217

  Li, Chao Jun ^a   Chen, Dong Li ^a   Lu, Yue Qi ^a   Haberman, John X ^a   Mague, Joel T ^a  

^a Tulane University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029991526     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960489p     Document Type: Article

References (34)

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20. For reviews, see: Li, C. J. Chem. Rev. 1993, 93, 2023. Li, C. J. Tetrahedron, in press. Chan, T. H. Pure Appl. Chem., in press. Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741. For other examples of indium-mediated reactions in aqueous media, see: Li, C. J.; Lu, Y. Q. Tetrahedron Lett. 1995, 36, 2721. Li, C. J. Tetrahedron Lett. 1995, 36, 517. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7071. Chan, T. H.; Li. C. J. J. Chem. Soc., Chem. Commun. 1992, 747. Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228. Araki, S.; Jin, S. J.; Idou, Y.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1992, 65, 1736. Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647. Gordon. D. M.; Whitesides, G. M. J. Org. Chem. 1993, 58, 7937. Gao, J.; Harter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714. Prenner, R. H.; Binder, W. H.; Schmid, W Liebigs Ann. Chem. 1994, 73. Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863.
21. For reviews, see: Li, C. J. Chem. Rev. 1993, 93, 2023. Li, C. J. Tetrahedron, in press. Chan, T. H. Pure Appl. Chem., in press. Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741. For other examples of indium-mediated reactions in aqueous media, see: Li, C. J.; Lu, Y. Q. Tetrahedron Lett. 1995, 36, 2721. Li, C. J. Tetrahedron Lett. 1995, 36, 517. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7071. Chan, T. H.; Li. C. J. J. Chem. Soc., Chem. Commun. 1992, 747. Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228. Araki, S.; Jin, S. J.; Idou, Y.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1992, 65, 1736. Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647. Gordon. D. M.; Whitesides, G. M. J. Org. Chem. 1993, 58, 7937. Gao, J.; Harter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714. Prenner, R. H.; Binder, W. H.; Schmid, W Liebigs Ann. Chem. 1994, 73. Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863.
22. For reviews, see: Li, C. J. Chem. Rev. 1993, 93, 2023. Li, C. J. Tetrahedron, in press. Chan, T. H. Pure Appl. Chem., in press. Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741. For other examples of indium-mediated reactions in aqueous media, see: Li, C. J.; Lu, Y. Q. Tetrahedron Lett. 1995, 36, 2721. Li, C. J. Tetrahedron Lett. 1995, 36, 517. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7071. Chan, T. H.; Li. C. J. J. Chem. Soc., Chem. Commun. 1992, 747. Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228. Araki, S.; Jin, S. J.; Idou, Y.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1992, 65, 1736. Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647. Gordon. D. M.; Whitesides, G. M. J. Org. Chem. 1993, 58, 7937. Gao, J.; Harter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714. Prenner, R. H.; Binder, W. H.; Schmid, W Liebigs Ann. Chem. 1994, 73. Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863.
23. For reviews, see: Li, C. J. Chem. Rev. 1993, 93, 2023. Li, C. J. Tetrahedron, in press. Chan, T. H. Pure Appl. Chem., in press. Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741. For other examples of indium-mediated reactions in aqueous media, see: Li, C. J.; Lu, Y. Q. Tetrahedron Lett. 1995, 36, 2721. Li, C. J. Tetrahedron Lett. 1995, 36, 517. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7071. Chan, T. H.; Li. C. J. J. Chem. Soc., Chem. Commun. 1992, 747. Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228. Araki, S.; Jin, S. J.; Idou, Y.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1992, 65, 1736. Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647. Gordon. D. M.; Whitesides, G. M. J. Org. Chem. 1993, 58, 7937. Gao, J.; Harter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714. Prenner, R. H.; Binder, W. H.; Schmid, W Liebigs Ann. Chem. 1994, 73. Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863.
24. For reviews, see: Li, C. J. Chem. Rev. 1993, 93, 2023. Li, C. J. Tetrahedron, in press. Chan, T. H. Pure Appl. Chem., in press. Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741. For other examples of indium-mediated reactions in aqueous media, see: Li, C. J.; Lu, Y. Q. Tetrahedron Lett. 1995, 36, 2721. Li, C. J. Tetrahedron Lett. 1995, 36, 517. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7071. Chan, T. H.; Li. C. J. J. Chem. Soc., Chem. Commun. 1992, 747. Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228. Araki, S.; Jin, S. J.; Idou, Y.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1992, 65, 1736. Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647. Gordon. D. M.; Whitesides, G. M. J. Org. Chem. 1993, 58, 7937. Gao, J.; Harter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714. Prenner, R. H.; Binder, W. H.; Schmid, W Liebigs Ann. Chem. 1994, 73. Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863.
25. For reviews, see: Li, C. J. Chem. Rev. 1993, 93, 2023. Li, C. J. Tetrahedron, in press. Chan, T. H. Pure Appl. Chem., in press. Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741. For other examples of indium-mediated reactions in aqueous media, see: Li, C. J.; Lu, Y. Q. Tetrahedron Lett. 1995, 36, 2721. Li, C. J. Tetrahedron Lett. 1995, 36, 517. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7071. Chan, T. H.; Li. C. J. J. Chem. Soc., Chem. Commun. 1992, 747. Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228. Araki, S.; Jin, S. J.; Idou, Y.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1992, 65, 1736. Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647. Gordon. D. M.; Whitesides, G. M. J. Org. Chem. 1993, 58, 7937. Gao, J.; Harter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714. Prenner, R. H.; Binder, W. H.; Schmid, W Liebigs Ann. Chem. 1994, 73. Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863.
26. For reviews, see: Li, C. J. Chem. Rev. 1993, 93, 2023. Li, C. J. Tetrahedron, in press. Chan, T. H. Pure Appl. Chem., in press. Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741. For other examples of indium-mediated reactions in aqueous media, see: Li, C. J.; Lu, Y. Q. Tetrahedron Lett. 1995, 36, 2721. Li, C. J. Tetrahedron Lett. 1995, 36, 517. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7071. Chan, T. H.; Li. C. J. J. Chem. Soc., Chem. Commun. 1992, 747. Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228. Araki, S.; Jin, S. J.; Idou, Y.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1992, 65, 1736. Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647. Gordon. D. M.; Whitesides, G. M. J. Org. Chem. 1993, 58, 7937. Gao, J.; Harter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714. Prenner, R. H.; Binder, W. H.; Schmid, W Liebigs Ann. Chem. 1994, 73. Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863.
27. For reviews, see: Li, C. J. Chem. Rev. 1993, 93, 2023. Li, C. J. Tetrahedron, in press. Chan, T. H. Pure Appl. Chem., in press. Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741. For other examples of indium-mediated reactions in aqueous media, see: Li, C. J.; Lu, Y. Q. Tetrahedron Lett. 1995, 36, 2721. Li, C. J. Tetrahedron Lett. 1995, 36, 517. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7071. Chan, T. H.; Li. C. J. J. Chem. Soc., Chem. Commun. 1992, 747. Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228. Araki, S.; Jin, S. J.; Idou, Y.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1992, 65, 1736. Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647. Gordon. D. M.; Whitesides, G. M. J. Org. Chem. 1993, 58, 7937. Gao, J.; Harter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714. Prenner, R. H.; Binder, W. H.; Schmid, W Liebigs Ann. Chem. 1994, 73. Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863.
28. For reviews, see: Li, C. J. Chem. Rev. 1993, 93, 2023. Li, C. J. Tetrahedron, in press. Chan, T. H. Pure Appl. Chem., in press. Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741. For other examples of indium-mediated reactions in aqueous media, see: Li, C. J.; Lu, Y. Q. Tetrahedron Lett. 1995, 36, 2721. Li, C. J. Tetrahedron Lett. 1995, 36, 517. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7071. Chan, T. H.; Li. C. J. J. Chem. Soc., Chem. Commun. 1992, 747. Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228. Araki, S.; Jin, S. J.; Idou, Y.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1992, 65, 1736. Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647. Gordon. D. M.; Whitesides, G. M. J. Org. Chem. 1993, 58, 7937. Gao, J.; Harter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714. Prenner, R. H.; Binder, W. H.; Schmid, W Liebigs Ann. Chem. 1994, 73. Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863.
29. For reviews, see: Li, C. J. Chem. Rev. 1993, 93, 2023. Li, C. J. Tetrahedron, in press. Chan, T. H. Pure Appl. Chem., in press. Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741. For other examples of indium-mediated reactions in aqueous media, see: Li, C. J.; Lu, Y. Q. Tetrahedron Lett. 1995, 36, 2721. Li, C. J. Tetrahedron Lett. 1995, 36, 517. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7071. Chan, T. H.; Li. C. J. J. Chem. Soc., Chem. Commun. 1992, 747. Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228. Araki, S.; Jin, S. J.; Idou, Y.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1992, 65, 1736. Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647. Gordon. D. M.; Whitesides, G. M. J. Org. Chem. 1993, 58, 7937. Gao, J.; Harter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714. Prenner, R. H.; Binder, W. H.; Schmid, W Liebigs Ann. Chem. 1994, 73. Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863.
30. For reviews, see: Li, C. J. Chem. Rev. 1993, 93, 2023. Li, C. J. Tetrahedron, in press. Chan, T. H. Pure Appl. Chem., in press. Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741. For other examples of indium-mediated reactions in aqueous media, see: Li, C. J.; Lu, Y. Q. Tetrahedron Lett. 1995, 36, 2721. Li, C. J. Tetrahedron Lett. 1995, 36, 517. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7071. Chan, T. H.; Li. C. J. J. Chem. Soc., Chem. Commun. 1992, 747. Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228. Araki, S.; Jin, S. J.; Idou, Y.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1992, 65, 1736. Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647. Gordon. D. M.; Whitesides, G. M. J. Org. Chem. 1993, 58, 7937. Gao, J.; Harter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714. Prenner, R. H.; Binder, W. H.; Schmid, W Liebigs Ann. Chem. 1994, 73. Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863.
31. For reviews, see: Li, C. J. Chem. Rev. 1993, 93, 2023. Li, C. J. Tetrahedron, in press. Chan, T. H. Pure Appl. Chem., in press. Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741. For other examples of indium-mediated reactions in aqueous media, see: Li, C. J.; Lu, Y. Q. Tetrahedron Lett. 1995, 36, 2721. Li, C. J. Tetrahedron Lett. 1995, 36, 517. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7071. Chan, T. H.; Li. C. J. J. Chem. Soc., Chem. Commun. 1992, 747. Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228. Araki, S.; Jin, S. J.; Idou, Y.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1992, 65, 1736. Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647. Gordon. D. M.; Whitesides, G. M. J. Org. Chem. 1993, 58, 7937. Gao, J.; Harter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714. Prenner, R. H.; Binder, W. H.; Schmid, W Liebigs Ann. Chem. 1994, 73. Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863.
32. For reviews, see: Li, C. J. Chem. Rev. 1993, 93, 2023. Li, C. J. Tetrahedron, in press. Chan, T. H. Pure Appl. Chem., in press. Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741. For other examples of indium-mediated reactions in aqueous media, see: Li, C. J.; Lu, Y. Q. Tetrahedron Lett. 1995, 36, 2721. Li, C. J. Tetrahedron Lett. 1995, 36, 517. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7071. Chan, T. H.; Li. C. J. J. Chem. Soc., Chem. Commun. 1992, 747. Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228. Araki, S.; Jin, S. J.; Idou, Y.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1992, 65, 1736. Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647. Gordon. D. M.; Whitesides, G. M. J. Org. Chem. 1993, 58, 7937. Gao, J.; Harter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714. Prenner, R. H.; Binder, W. H.; Schmid, W Liebigs Ann. Chem. 1994, 73. Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863.
33. A typical experimental procedure in as follows: To a mixture of 1 (289 mg, 1 mmol) in 10 mL of aqueous 0.1 N HCl/methanol (3:1) was added indium powder (230 mg, 2 mmol). The reaction mixture was vigorously stirred at room temperature for 10 h, quenched with 1 N HCl (1 mL) aqueous solution, extracted with 10 mL of ether (3x). The combined organic phases were dried over magnesium suflate and concentrated. The residue was then mixed with DBU (304 mg, 2 mmol) in 10 mL THF. The mixture was stirred overnight at room temperature. Workup followed by column chramatography on silica gel provided 3 (105.6 mg, overall yield 50%).
34. w = 0.060, GOF = 2.01 for 1475 observations with I ≥ 3σ(I).