Cycloaddition of cyclopentadiene to 3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose. Synthesis and representative chemistry of 1,6-anhydro-2,3-dideoxy-β-D-glycero-hex-2-enopyran-4-ulose ("isolevoglucosenone")

Journal of Organic Chemistry

Volumn 61, Issue 11, 1996, Pages 3783-3793

  Horton, Derek ^a   Roski, James P ^a,b   Norris, Peter ^a,c  

^a AMERICAN UNIVERSITY   (United States)

^b LUBRIZOL CORPORATION   (United States)

^c YOUNGSTOWN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000716447     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960032y     Document Type: Article

References (65)

1. For general references, see: Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergammon: New York, 1983. Inch, T. D. Tetrahedron 1984, 40, 3161. Fraser-Reid, B.; Anderson, R. C. Carbohydrate Derivatives in the Asymmetric Synthesis of Natural Products, Fortschr. Chem. Org. Naturst. 1980, 1. Lichtenthaler, F. W. Pure Appl. Chem. 1978, 50, 1342. For selected applications in the total synthesis of natural products, see: Wu, W.-L.; Wu, Y.-L. J. Org. Chem. 1993, 58, 2760. McIntosh, M. C.; Weinreb, S. M. J. Org. Chem. 1993, 58, 4823. Hanessian, S.; Sahoo, S. P.; Botta, M. Tetrahedron Lett. 1987, 28, 1143, 1147, 1151. Li, W.-R.; Han, S.-Y.; Joullié, M. M. Tetrahedron Lett. 1992, 33, 3595. Bruns, W.; Horns, F.; Redlich, H. Synthesis 1995, 335. Chen, S.-H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 5834. Nicolaou, K. C.; Nugiel, D. A.; Couladouros, E.; Hwang, C.-K. Tetrahedron 1990, 46, 4517. Nicolaou, K. C.; Tiebes, J.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Sato, M.; Unterstellar, E. J. Am. Chem. Soc. 1994, 116, 9371.
2. For general references, see: Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergammon: New York, 1983. Inch, T. D. Tetrahedron 1984, 40, 3161. Fraser-Reid, B.; Anderson, R. C. Carbohydrate Derivatives in the Asymmetric Synthesis of Natural Products, Fortschr. Chem. Org. Naturst. 1980, 1. Lichtenthaler, F. W. Pure Appl. Chem. 1978, 50, 1342. For selected applications in the total synthesis of natural products, see: Wu, W.-L.; Wu, Y.-L. J. Org. Chem. 1993, 58, 2760. McIntosh, M. C.; Weinreb, S. M. J. Org. Chem. 1993, 58, 4823. Hanessian, S.; Sahoo, S. P.; Botta, M. Tetrahedron Lett. 1987, 28, 1143, 1147, 1151. Li, W.-R.; Han, S.-Y.; Joullié, M. M. Tetrahedron Lett. 1992, 33, 3595. Bruns, W.; Horns, F.; Redlich, H. Synthesis 1995, 335. Chen, S.-H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 5834. Nicolaou, K. C.; Nugiel, D. A.; Couladouros, E.; Hwang, C.-K. Tetrahedron 1990, 46, 4517. Nicolaou, K. C.; Tiebes, J.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Sato, M.; Unterstellar, E. J. Am. Chem. Soc. 1994, 116, 9371.
3. For general references, see: Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergammon: New York, 1983. Inch, T. D. Tetrahedron 1984, 40, 3161. Fraser-Reid, B.; Anderson, R. C. Carbohydrate Derivatives in the Asymmetric Synthesis of Natural Products, Fortschr. Chem. Org. Naturst. 1980, 1. Lichtenthaler, F. W. Pure Appl. Chem. 1978, 50, 1342. For selected applications in the total synthesis of natural products, see: Wu, W.-L.; Wu, Y.-L. J. Org. Chem. 1993, 58, 2760. McIntosh, M. C.; Weinreb, S. M. J. Org. Chem. 1993, 58, 4823. Hanessian, S.; Sahoo, S. P.; Botta, M. Tetrahedron Lett. 1987, 28, 1143, 1147, 1151. Li, W.-R.; Han, S.-Y.; Joullié, M. M. Tetrahedron Lett. 1992, 33, 3595. Bruns, W.; Horns, F.; Redlich, H. Synthesis 1995, 335. Chen, S.-H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 5834. Nicolaou, K. C.; Nugiel, D. A.; Couladouros, E.; Hwang, C.-K. Tetrahedron 1990, 46, 4517. Nicolaou, K. C.; Tiebes, J.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Sato, M.; Unterstellar, E. J. Am. Chem. Soc. 1994, 116, 9371.
4. For general references, see: Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergammon: New York, 1983. Inch, T. D. Tetrahedron 1984, 40, 3161. Fraser-Reid, B.; Anderson, R. C. Carbohydrate Derivatives in the Asymmetric Synthesis of Natural Products, Fortschr. Chem. Org. Naturst. 1980, 1. Lichtenthaler, F. W. Pure Appl. Chem. 1978, 50, 1342. For selected applications in the total synthesis of natural products, see: Wu, W.-L.; Wu, Y.-L. J. Org. Chem. 1993, 58, 2760. McIntosh, M. C.; Weinreb, S. M. J. Org. Chem. 1993, 58, 4823. Hanessian, S.; Sahoo, S. P.; Botta, M. Tetrahedron Lett. 1987, 28, 1143, 1147, 1151. Li, W.-R.; Han, S.-Y.; Joullié, M. M. Tetrahedron Lett. 1992, 33, 3595. Bruns, W.; Horns, F.; Redlich, H. Synthesis 1995, 335. Chen, S.-H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 5834. Nicolaou, K. C.; Nugiel, D. A.; Couladouros, E.; Hwang, C.-K. Tetrahedron 1990, 46, 4517. Nicolaou, K. C.; Tiebes, J.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Sato, M.; Unterstellar, E. J. Am. Chem. Soc. 1994, 116, 9371.
5. For general references, see: Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergammon: New York, 1983. Inch, T. D. Tetrahedron 1984, 40, 3161. Fraser-Reid, B.; Anderson, R. C. Carbohydrate Derivatives in the Asymmetric Synthesis of Natural Products, Fortschr. Chem. Org. Naturst. 1980, 1. Lichtenthaler, F. W. Pure Appl. Chem. 1978, 50, 1342. For selected applications in the total synthesis of natural products, see: Wu, W.-L.; Wu, Y.-L. J. Org. Chem. 1993, 58, 2760. McIntosh, M. C.; Weinreb, S. M. J. Org. Chem. 1993, 58, 4823. Hanessian, S.; Sahoo, S. P.; Botta, M. Tetrahedron Lett. 1987, 28, 1143, 1147, 1151. Li, W.-R.; Han, S.-Y.; Joullié, M. M. Tetrahedron Lett. 1992, 33, 3595. Bruns, W.; Horns, F.; Redlich, H. Synthesis 1995, 335. Chen, S.-H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 5834. Nicolaou, K. C.; Nugiel, D. A.; Couladouros, E.; Hwang, C.-K. Tetrahedron 1990, 46, 4517. Nicolaou, K. C.; Tiebes, J.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Sato, M.; Unterstellar, E. J. Am. Chem. Soc. 1994, 116, 9371.
6. For general references, see: Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergammon: New York, 1983. Inch, T. D. Tetrahedron 1984, 40, 3161. Fraser-Reid, B.; Anderson, R. C. Carbohydrate Derivatives in the Asymmetric Synthesis of Natural Products, Fortschr. Chem. Org. Naturst. 1980, 1. Lichtenthaler, F. W. Pure Appl. Chem. 1978, 50, 1342. For selected applications in the total synthesis of natural products, see: Wu, W.-L.; Wu, Y.-L. J. Org. Chem. 1993, 58, 2760. McIntosh, M. C.; Weinreb, S. M. J. Org. Chem. 1993, 58, 4823. Hanessian, S.; Sahoo, S. P.; Botta, M. Tetrahedron Lett. 1987, 28, 1143, 1147, 1151. Li, W.-R.; Han, S.-Y.; Joullié, M. M. Tetrahedron Lett. 1992, 33, 3595. Bruns, W.; Horns, F.; Redlich, H. Synthesis 1995, 335. Chen, S.-H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 5834. Nicolaou, K. C.; Nugiel, D. A.; Couladouros, E.; Hwang, C.-K. Tetrahedron 1990, 46, 4517. Nicolaou, K. C.; Tiebes, J.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Sato, M.; Unterstellar, E. J. Am. Chem. Soc. 1994, 116, 9371.
7. For general references, see: Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergammon: New York, 1983. Inch, T. D. Tetrahedron 1984, 40, 3161. Fraser-Reid, B.; Anderson, R. C. Carbohydrate Derivatives in the Asymmetric Synthesis of Natural Products, Fortschr. Chem. Org. Naturst. 1980, 1. Lichtenthaler, F. W. Pure Appl. Chem. 1978, 50, 1342. For selected applications in the total synthesis of natural products, see: Wu, W.-L.; Wu, Y.-L. J. Org. Chem. 1993, 58, 2760. McIntosh, M. C.; Weinreb, S. M. J. Org. Chem. 1993, 58, 4823. Hanessian, S.; Sahoo, S. P.; Botta, M. Tetrahedron Lett. 1987, 28, 1143, 1147, 1151. Li, W.-R.; Han, S.-Y.; Joullié, M. M. Tetrahedron Lett. 1992, 33, 3595. Bruns, W.; Horns, F.; Redlich, H. Synthesis 1995, 335. Chen, S.-H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 5834. Nicolaou, K. C.; Nugiel, D. A.; Couladouros, E.; Hwang, C.-K. Tetrahedron 1990, 46, 4517. Nicolaou, K. C.; Tiebes, J.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Sato, M.; Unterstellar, E. J. Am. Chem. Soc. 1994, 116, 9371.
8. For general references, see: Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergammon: New York, 1983. Inch, T. D. Tetrahedron 1984, 40, 3161. Fraser-Reid, B.; Anderson, R. C. Carbohydrate Derivatives in the Asymmetric Synthesis of Natural Products, Fortschr. Chem. Org. Naturst. 1980, 1. Lichtenthaler, F. W. Pure Appl. Chem. 1978, 50, 1342. For selected applications in the total synthesis of natural products, see: Wu, W.-L.; Wu, Y.-L. J. Org. Chem. 1993, 58, 2760. McIntosh, M. C.; Weinreb, S. M. J. Org. Chem. 1993, 58, 4823. Hanessian, S.; Sahoo, S. P.; Botta, M. Tetrahedron Lett. 1987, 28, 1143, 1147, 1151. Li, W.-R.; Han, S.-Y.; Joullié, M. M. Tetrahedron Lett. 1992, 33, 3595. Bruns, W.; Horns, F.; Redlich, H. Synthesis 1995, 335. Chen, S.-H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 5834. Nicolaou, K. C.; Nugiel, D. A.; Couladouros, E.; Hwang, C.-K. Tetrahedron 1990, 46, 4517. Nicolaou, K. C.; Tiebes, J.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Sato, M.; Unterstellar, E. J. Am. Chem. Soc. 1994, 116, 9371.
9. For general references, see: Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergammon: New York, 1983. Inch, T. D. Tetrahedron 1984, 40, 3161. Fraser-Reid, B.; Anderson, R. C. Carbohydrate Derivatives in the Asymmetric Synthesis of Natural Products, Fortschr. Chem. Org. Naturst. 1980, 1. Lichtenthaler, F. W. Pure Appl. Chem. 1978, 50, 1342. For selected applications in the total synthesis of natural products, see: Wu, W.-L.; Wu, Y.-L. J. Org. Chem. 1993, 58, 2760. McIntosh, M. C.; Weinreb, S. M. J. Org. Chem. 1993, 58, 4823. Hanessian, S.; Sahoo, S. P.; Botta, M. Tetrahedron Lett. 1987, 28, 1143, 1147, 1151. Li, W.-R.; Han, S.-Y.; Joullié, M. M. Tetrahedron Lett. 1992, 33, 3595. Bruns, W.; Horns, F.; Redlich, H. Synthesis 1995, 335. Chen, S.-H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 5834. Nicolaou, K. C.; Nugiel, D. A.; Couladouros, E.; Hwang, C.-K. Tetrahedron 1990, 46, 4517. Nicolaou, K. C.; Tiebes, J.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Sato, M.; Unterstellar, E. J. Am. Chem. Soc. 1994, 116, 9371.
10. For general references, see: Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergammon: New York, 1983. Inch, T. D. Tetrahedron 1984, 40, 3161. Fraser-Reid, B.; Anderson, R. C. Carbohydrate Derivatives in the Asymmetric Synthesis of Natural Products, Fortschr. Chem. Org. Naturst. 1980, 1. Lichtenthaler, F. W. Pure Appl. Chem. 1978, 50, 1342. For selected applications in the total synthesis of natural products, see: Wu, W.-L.; Wu, Y.-L. J. Org. Chem. 1993, 58, 2760. McIntosh, M. C.; Weinreb, S. M. J. Org. Chem. 1993, 58, 4823. Hanessian, S.; Sahoo, S. P.; Botta, M. Tetrahedron Lett. 1987, 28, 1143, 1147, 1151. Li, W.-R.; Han, S.-Y.; Joullié, M. M. Tetrahedron Lett. 1992, 33, 3595. Bruns, W.; Horns, F.; Redlich, H. Synthesis 1995, 335. Chen, S.-H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 5834. Nicolaou, K. C.; Nugiel, D. A.; Couladouros, E.; Hwang, C.-K. Tetrahedron 1990, 46, 4517. Nicolaou, K. C.; Tiebes, J.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Sato, M.; Unterstellar, E. J. Am. Chem. Soc. 1994, 116, 9371.
11. For general references, see: Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergammon: New York, 1983. Inch, T. D. Tetrahedron 1984, 40, 3161. Fraser-Reid, B.; Anderson, R. C. Carbohydrate Derivatives in the Asymmetric Synthesis of Natural Products, Fortschr. Chem. Org. Naturst. 1980, 1. Lichtenthaler, F. W. Pure Appl. Chem. 1978, 50, 1342. For selected applications in the total synthesis of natural products, see: Wu, W.-L.; Wu, Y.-L. J. Org. Chem. 1993, 58, 2760. McIntosh, M. C.; Weinreb, S. M. J. Org. Chem. 1993, 58, 4823. Hanessian, S.; Sahoo, S. P.; Botta, M. Tetrahedron Lett. 1987, 28, 1143, 1147, 1151. Li, W.-R.; Han, S.-Y.; Joullié, M. M. Tetrahedron Lett. 1992, 33, 3595. Bruns, W.; Horns, F.; Redlich, H. Synthesis 1995, 335. Chen, S.-H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 5834. Nicolaou, K. C.; Nugiel, D. A.; Couladouros, E.; Hwang, C.-K. Tetrahedron 1990, 46, 4517. Nicolaou, K. C.; Tiebes, J.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Sato, M.; Unterstellar, E. J. Am. Chem. Soc. 1994, 116, 9371.
12. For general references, see: Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergammon: New York, 1983. Inch, T. D. Tetrahedron 1984, 40, 3161. Fraser-Reid, B.; Anderson, R. C. Carbohydrate Derivatives in the Asymmetric Synthesis of Natural Products, Fortschr. Chem. Org. Naturst. 1980, 1. Lichtenthaler, F. W. Pure Appl. Chem. 1978, 50, 1342. For selected applications in the total synthesis of natural products, see: Wu, W.-L.; Wu, Y.-L. J. Org. Chem. 1993, 58, 2760. McIntosh, M. C.; Weinreb, S. M. J. Org. Chem. 1993, 58, 4823. Hanessian, S.; Sahoo, S. P.; Botta, M. Tetrahedron Lett. 1987, 28, 1143, 1147, 1151. Li, W.-R.; Han, S.-Y.; Joullié, M. M. Tetrahedron Lett. 1992, 33, 3595. Bruns, W.; Horns, F.; Redlich, H. Synthesis 1995, 335. Chen, S.-H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 5834. Nicolaou, K. C.; Nugiel, D. A.; Couladouros, E.; Hwang, C.-K. Tetrahedron 1990, 46, 4517. Nicolaou, K. C.; Tiebes, J.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Sato, M.; Unterstellar, E. J. Am. Chem. Soc. 1994, 116, 9371.
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54. The crystal structure analysis of compound 15 was performed by Dr. Judith Gallucci of the Department of Chemistry at The Ohio State University using the following programs: TEXSAN, TEXRAY Structural Analysis Package, version 2.1, by Molecular Structure Corporation, College Station, Texas, 1987; MITHRIL, A Computer Program for the Automatic Solution of Crystal Structures from X-ray Data, by C. J. Gilmore, University of Glasgow, Scotland, 1983.
55. The crystal structure analysis of compound 15 was performed by Dr. Judith Gallucci of the Department of Chemistry at The Ohio State University using the following programs: TEXSAN, TEXRAY Structural Analysis Package, version 2.1, by Molecular Structure Corporation, College Station, Texas, 1987; MITHRIL, A Computer Program for the Automatic Solution of Crystal Structures from X-ray Data, by C. J. Gilmore, University of Glasgow, Scotland, 1983.
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65. The author has deposited atomic coordinates for compound 15 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.