A One-Pot Condensation of Pyrones and Enals. Synthesis of 1H,7H-5a,6,8,9-Tetrahydro-1-oxopyrano[4,3-6][1]benzopyrans

Journal of Organic Chemistry

Volumn 62, Issue 20, 1997, Pages 6888-6896

  Hua, Duy H ^a   Chen, Yi ^a   Sin, Hong Sig ^a   Maroto, Maria J ^a   Robinson, Paul D ^a,b   Newell, Steven W ^a   Perchellet, Elisabeth M ^a   Ladesich, James B ^a   Freeman, Jonathan A ^a   Perchellet, Jean Pierre ^a   Chiang, Peter K ^a,c  

^a KANSAS STATE UNIVERSITY   (United States)

^b SOUTHERN ILLINOIS UNIVERSITY   (United States)

^c WALTER REED ARMY INSTITUTE OF RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001081027     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970642d     Document Type: Article

References (34)

1. With enones and enals: (a) de March, P.; Moreno-Manas, M.; Pleixats, R.; Roca, J. L. J. Heterocycl. Chem. 1984, 21, 1369-1370 and references cited therein. (b) de March, P.; Moreno-Manas, M.; Casado, J.; Pleixats, R.; Roca, J. L.; Trius, A. J. Heterocycl. Chem., 1984, 21, 85-89. With aldehydes: (c) Cervera, M.; Moreno-Manas, M.; Pleixats, R. Tetrahedron 1990, 46, 7885-7892. (d) Moreno-Manas, M.; Papell, E.; Pleixats, R.; Ribas, J.; Virgili, A. J. Heterocycl. Chem. 1986, 23, 413-416. (e) Moreno-Manas, M.; Pleixats, R. Synthesis 1984, 430-431. (f) de March, P.; Moreno-Manas, M.; Roca, J. L. J. Heterocycl. Chem. 1984, 21, 1371-1372. (g) de March, P.; Moreno-Manas, M.; Pi, R.; Trius, A. J. Heterocycl. Chem. 1982, 19, 335-336.
2. With enones and enals: (a) de March, P.; Moreno-Manas, M.; Pleixats, R.; Roca, J. L. J. Heterocycl. Chem. 1984, 21, 1369-1370 and references cited therein. (b) de March, P.; Moreno-Manas, M.; Casado, J.; Pleixats, R.; Roca, J. L.; Trius, A. J. Heterocycl. Chem., 1984, 21, 85-89. With aldehydes: (c) Cervera, M.; Moreno-Manas, M.; Pleixats, R. Tetrahedron 1990, 46, 7885-7892. (d) Moreno-Manas, M.; Papell, E.; Pleixats, R.; Ribas, J.; Virgili, A. J. Heterocycl. Chem. 1986, 23, 413-416. (e) Moreno-Manas, M.; Pleixats, R. Synthesis 1984, 430-431. (f) de March, P.; Moreno-Manas, M.; Roca, J. L. J. Heterocycl. Chem. 1984, 21, 1371-1372. (g) de March, P.; Moreno-Manas, M.; Pi, R.; Trius, A. J. Heterocycl. Chem. 1982, 19, 335-336.
3. With enones and enals: (a) de March, P.; Moreno-Manas, M.; Pleixats, R.; Roca, J. L. J. Heterocycl. Chem. 1984, 21, 1369-1370 and references cited therein. (b) de March, P.; Moreno-Manas, M.; Casado, J.; Pleixats, R.; Roca, J. L.; Trius, A. J. Heterocycl. Chem., 1984, 21, 85-89. With aldehydes: (c) Cervera, M.; Moreno-Manas, M.; Pleixats, R. Tetrahedron 1990, 46, 7885-7892. (d) Moreno-Manas, M.; Papell, E.; Pleixats, R.; Ribas, J.; Virgili, A. J. Heterocycl. Chem. 1986, 23, 413-416. (e) Moreno-Manas, M.; Pleixats, R. Synthesis 1984, 430-431. (f) de March, P.; Moreno-Manas, M.; Roca, J. L. J. Heterocycl. Chem. 1984, 21, 1371-1372. (g) de March, P.; Moreno-Manas, M.; Pi, R.; Trius, A. J. Heterocycl. Chem. 1982, 19, 335-336.
4. With enones and enals: (a) de March, P.; Moreno-Manas, M.; Pleixats, R.; Roca, J. L. J. Heterocycl. Chem. 1984, 21, 1369-1370 and references cited therein. (b) de March, P.; Moreno-Manas, M.; Casado, J.; Pleixats, R.; Roca, J. L.; Trius, A. J. Heterocycl. Chem., 1984, 21, 85-89. With aldehydes: (c) Cervera, M.; Moreno-Manas, M.; Pleixats, R. Tetrahedron 1990, 46, 7885-7892. (d) Moreno-Manas, M.; Papell, E.; Pleixats, R.; Ribas, J.; Virgili, A. J. Heterocycl. Chem. 1986, 23, 413-416. (e) Moreno-Manas, M.; Pleixats, R. Synthesis 1984, 430-431. (f) de March, P.; Moreno-Manas, M.; Roca, J. L. J. Heterocycl. Chem. 1984, 21, 1371-1372. (g) de March, P.; Moreno-Manas, M.; Pi, R.; Trius, A. J. Heterocycl. Chem. 1982, 19, 335-336.
5. With enones and enals: (a) de March, P.; Moreno-Manas, M.; Pleixats, R.; Roca, J. L. J. Heterocycl. Chem. 1984, 21, 1369-1370 and references cited therein. (b) de March, P.; Moreno-Manas, M.; Casado, J.; Pleixats, R.; Roca, J. L.; Trius, A. J. Heterocycl. Chem., 1984, 21, 85-89. With aldehydes: (c) Cervera, M.; Moreno-Manas, M.; Pleixats, R. Tetrahedron 1990, 46, 7885-7892. (d) Moreno-Manas, M.; Papell, E.; Pleixats, R.; Ribas, J.; Virgili, A. J. Heterocycl. Chem. 1986, 23, 413-416. (e) Moreno-Manas, M.; Pleixats, R. Synthesis 1984, 430-431. (f) de March, P.; Moreno-Manas, M.; Roca, J. L. J. Heterocycl. Chem. 1984, 21, 1371-1372. (g) de March, P.; Moreno-Manas, M.; Pi, R.; Trius, A. J. Heterocycl. Chem. 1982, 19, 335-336.
6. With enones and enals: (a) de March, P.; Moreno-Manas, M.; Pleixats, R.; Roca, J. L. J. Heterocycl. Chem. 1984, 21, 1369-1370 and references cited therein. (b) de March, P.; Moreno-Manas, M.; Casado, J.; Pleixats, R.; Roca, J. L.; Trius, A. J. Heterocycl. Chem., 1984, 21, 85-89. With aldehydes: (c) Cervera, M.; Moreno-Manas, M.; Pleixats, R. Tetrahedron 1990, 46, 7885-7892. (d) Moreno-Manas, M.; Papell, E.; Pleixats, R.; Ribas, J.; Virgili, A. J. Heterocycl. Chem. 1986, 23, 413-416. (e) Moreno-Manas, M.; Pleixats, R. Synthesis 1984, 430-431. (f) de March, P.; Moreno-Manas, M.; Roca, J. L. J. Heterocycl. Chem. 1984, 21, 1371-1372. (g) de March, P.; Moreno-Manas, M.; Pi, R.; Trius, A. J. Heterocycl. Chem. 1982, 19, 335-336.
7. With enones and enals: (a) de March, P.; Moreno-Manas, M.; Pleixats, R.; Roca, J. L. J. Heterocycl. Chem. 1984, 21, 1369-1370 and references cited therein. (b) de March, P.; Moreno-Manas, M.; Casado, J.; Pleixats, R.; Roca, J. L.; Trius, A. J. Heterocycl. Chem., 1984, 21, 85-89. With aldehydes: (c) Cervera, M.; Moreno-Manas, M.; Pleixats, R. Tetrahedron 1990, 46, 7885-7892. (d) Moreno-Manas, M.; Papell, E.; Pleixats, R.; Ribas, J.; Virgili, A. J. Heterocycl. Chem. 1986, 23, 413-416. (e) Moreno-Manas, M.; Pleixats, R. Synthesis 1984, 430-431. (f) de March, P.; Moreno-Manas, M.; Roca, J. L. J. Heterocycl. Chem. 1984, 21, 1371-1372. (g) de March, P.; Moreno-Manas, M.; Pi, R.; Trius, A. J. Heterocycl. Chem. 1982, 19, 335-336.
8. With enones: (a) Hutchinson, D. W.; Tomlinson, J. A. Tetrahedron Lett. 1968, 48, 5027-5028. (b) Ikawa, M.; Stahmann, M. A.; Link, K. P. J. Am. Chem. Soc. 1944, 66, 902-909. (c) Seidman, M.; Link, K. P. J. Am. Chem. Soc. 1952, 74, 1885-1886. (d) Seidman, M.; Robertson, D. N.; Link, K. P. J. Am. Chem. Soc. 1950, 72, 5193-5194.
9. With enones: (a) Hutchinson, D. W.; Tomlinson, J. A. Tetrahedron Lett. 1968, 48, 5027-5028. (b) Ikawa, M.; Stahmann, M. A.; Link, K. P. J. Am. Chem. Soc. 1944, 66, 902-909. (c) Seidman, M.; Link, K. P. J. Am. Chem. Soc. 1952, 74, 1885-1886. (d) Seidman, M.; Robertson, D. N.; Link, K. P. J. Am. Chem. Soc. 1950, 72, 5193-5194.
10. With enones: (a) Hutchinson, D. W.; Tomlinson, J. A. Tetrahedron Lett. 1968, 48, 5027-5028. (b) Ikawa, M.; Stahmann, M. A.; Link, K. P. J. Am. Chem. Soc. 1944, 66, 902-909. (c) Seidman, M.; Link, K. P. J. Am. Chem. Soc. 1952, 74, 1885-1886. (d) Seidman, M.; Robertson, D. N.; Link, K. P. J. Am. Chem. Soc. 1950, 72, 5193-5194.
11. With enones: (a) Hutchinson, D. W.; Tomlinson, J. A. Tetrahedron Lett. 1968, 48, 5027-5028. (b) Ikawa, M.; Stahmann, M. A.; Link, K. P. J. Am. Chem. Soc. 1944, 66, 902-909. (c) Seidman, M.; Link, K. P. J. Am. Chem. Soc. 1952, 74, 1885-1886. (d) Seidman, M.; Robertson, D. N.; Link, K. P. J. Am. Chem. Soc. 1950, 72, 5193-5194.
12. Isolation: (a) Omura, S.; Tomoda, H.; Kim, Y. K.; Nishida, H. J. Antibiot. 1993, 46, 1168-1169. (b) Tomoda, H.; Kim, Y. K.; Nishida, H.; Masuma, R.; Omura, S. J. Antibiot. 1994, 47, 148-153. Structure of (+)-pyripyropene A: (c) Tomoda, H.; Nishida, H.; Kim, Y. K.; Obata, R.; Sunazuka, T.; Omura, S.; Bordner, J.; Guadliana, M.; Dormer, P. G.; Smith, A. B., III. J. Am. Chem. Soc. 1994, 116, 12097-12098. Synthesis of (+)-pyripyropene A: (d) Nagamitsu, T.; Sunazuka, T.; Obata, R.; Tomoda, H.; Tanaka, H.; Harigaya, Y.; Omura, S.; Smith, A. B., III. J. Org. Chem. 1995, 60, 8126-8127. Synthesis of (±)-GERI-BP001: (e) Parker, K. A.; Resnick, L. J. Org. Chem. 1995, 60, 5726-5728. Synthesis of (+)-pyripyropene E: (f) Smith, A. B., III; Kinsho, T.; Sunazuka, T.; Omura, S. Tetrahedron Lett. 1996, 37, 6461-6464.
13. Isolation: (a) Omura, S.; Tomoda, H.; Kim, Y. K.; Nishida, H. J. Antibiot. 1993, 46, 1168-1169. (b) Tomoda, H.; Kim, Y. K.; Nishida, H.; Masuma, R.; Omura, S. J. Antibiot. 1994, 47, 148-153. Structure of (+)-pyripyropene A: (c) Tomoda, H.; Nishida, H.; Kim, Y. K.; Obata, R.; Sunazuka, T.; Omura, S.; Bordner, J.; Guadliana, M.; Dormer, P. G.; Smith, A. B., III. J. Am. Chem. Soc. 1994, 116, 12097-12098. Synthesis of (+)-pyripyropene A: (d) Nagamitsu, T.; Sunazuka, T.; Obata, R.; Tomoda, H.; Tanaka, H.; Harigaya, Y.; Omura, S.; Smith, A. B., III. J. Org. Chem. 1995, 60, 8126-8127. Synthesis of (±)-GERI-BP001: (e) Parker, K. A.; Resnick, L. J. Org. Chem. 1995, 60, 5726-5728. Synthesis of (+)-pyripyropene E: (f) Smith, A. B., III; Kinsho, T.; Sunazuka, T.; Omura, S. Tetrahedron Lett. 1996, 37, 6461-6464.
14. Isolation: (a) Omura, S.; Tomoda, H.; Kim, Y. K.; Nishida, H. J. Antibiot. 1993, 46, 1168-1169. (b) Tomoda, H.; Kim, Y. K.; Nishida, H.; Masuma, R.; Omura, S. J. Antibiot. 1994, 47, 148-153. Structure of (+)-pyripyropene A: (c) Tomoda, H.; Nishida, H.; Kim, Y. K.; Obata, R.; Sunazuka, T.; Omura, S.; Bordner, J.; Guadliana, M.; Dormer, P. G.; Smith, A. B., III. J. Am. Chem. Soc. 1994, 116, 12097-12098. Synthesis of (+)-pyripyropene A: (d) Nagamitsu, T.; Sunazuka, T.; Obata, R.; Tomoda, H.; Tanaka, H.; Harigaya, Y.; Omura, S.; Smith, A. B., III. J. Org. Chem. 1995, 60, 8126-8127. Synthesis of (±)-GERI-BP001: (e) Parker, K. A.; Resnick, L. J. Org. Chem. 1995, 60, 5726-5728. Synthesis of (+)-pyripyropene E: (f) Smith, A. B., III; Kinsho, T.; Sunazuka, T.; Omura, S. Tetrahedron Lett. 1996, 37, 6461-6464.
15. Isolation: (a) Omura, S.; Tomoda, H.; Kim, Y. K.; Nishida, H. J. Antibiot. 1993, 46, 1168-1169. (b) Tomoda, H.; Kim, Y. K.; Nishida, H.; Masuma, R.; Omura, S. J. Antibiot. 1994, 47, 148-153. Structure of (+)-pyripyropene A: (c) Tomoda, H.; Nishida, H.; Kim, Y. K.; Obata, R.; Sunazuka, T.; Omura, S.; Bordner, J.; Guadliana, M.; Dormer, P. G.; Smith, A. B., III. J. Am. Chem. Soc. 1994, 116, 12097-12098. Synthesis of (+)-pyripyropene A: (d) Nagamitsu, T.; Sunazuka, T.; Obata, R.; Tomoda, H.; Tanaka, H.; Harigaya, Y.; Omura, S.; Smith, A. B., III. J. Org. Chem. 1995, 60, 8126-8127. Synthesis of (±)-GERI-BP001: (e) Parker, K. A.; Resnick, L. J. Org. Chem. 1995, 60, 5726-5728. Synthesis of (+)-pyripyropene E: (f) Smith, A. B., III; Kinsho, T.; Sunazuka, T.; Omura, S. Tetrahedron Lett. 1996, 37, 6461-6464.
16. Isolation: (a) Omura, S.; Tomoda, H.; Kim, Y. K.; Nishida, H. J. Antibiot. 1993, 46, 1168-1169. (b) Tomoda, H.; Kim, Y. K.; Nishida, H.; Masuma, R.; Omura, S. J. Antibiot. 1994, 47, 148-153. Structure of (+)-pyripyropene A: (c) Tomoda, H.; Nishida, H.; Kim, Y. K.; Obata, R.; Sunazuka, T.; Omura, S.; Bordner, J.; Guadliana, M.; Dormer, P. G.; Smith, A. B., III. J. Am. Chem. Soc. 1994, 116, 12097-12098. Synthesis of (+)-pyripyropene A: (d) Nagamitsu, T.; Sunazuka, T.; Obata, R.; Tomoda, H.; Tanaka, H.; Harigaya, Y.; Omura, S.; Smith, A. B., III. J. Org. Chem. 1995, 60, 8126-8127. Synthesis of (±)-GERI-BP001: (e) Parker, K. A.; Resnick, L. J. Org. Chem. 1995, 60, 5726-5728. Synthesis of (+)-pyripyropene E: (f) Smith, A. B., III; Kinsho, T.; Sunazuka, T.; Omura, S. Tetrahedron Lett. 1996, 37, 6461-6464.
17. Isolation: (a) Omura, S.; Tomoda, H.; Kim, Y. K.; Nishida, H. J. Antibiot. 1993, 46, 1168-1169. (b) Tomoda, H.; Kim, Y. K.; Nishida, H.; Masuma, R.; Omura, S. J. Antibiot. 1994, 47, 148-153. Structure of (+)-pyripyropene A: (c) Tomoda, H.; Nishida, H.; Kim, Y. K.; Obata, R.; Sunazuka, T.; Omura, S.; Bordner, J.; Guadliana, M.; Dormer, P. G.; Smith, A. B., III. J. Am. Chem. Soc. 1994, 116, 12097-12098. Synthesis of (+)-pyripyropene A: (d) Nagamitsu, T.; Sunazuka, T.; Obata, R.; Tomoda, H.; Tanaka, H.; Harigaya, Y.; Omura, S.; Smith, A. B., III. J. Org. Chem. 1995, 60, 8126-8127. Synthesis of (±)-GERI-BP001: (e) Parker, K. A.; Resnick, L. J. Org. Chem. 1995, 60, 5726-5728. Synthesis of (+)-pyripyropene E: (f) Smith, A. B., III; Kinsho, T.; Sunazuka, T.; Omura, S. Tetrahedron Lett. 1996, 37, 6461-6464.
18. Isolation and biological activities: (a) Omura, S.; Kuno, F.; Otoguro, Sunazuka, T.; Shiomi, K.; Masuma, R.; Iwai, Y. J. Antibiot. 1995, 48, 745-746. (b) Kuno, F.; Otoguro, K.; Shiomi, K.; Iwai, Y.; Omura, S. J. Antibiot. 1996, 49, 742-747.
19. Isolation and biological activities: (a) Omura, S.; Kuno, F.; Otoguro, Sunazuka, T.; Shiomi, K.; Masuma, R.; Iwai, Y. J. Antibiot. 1995, 48, 745-746. (b) Kuno, F.; Otoguro, K.; Shiomi, K.; Iwai, Y.; Omura, S. J. Antibiot. 1996, 49, 742-747.
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22. The asymmetric unit contains two nearly identical molecules with a = 8.8552(16) Å, 6 = 18.977(4) Å, c = 6.7869(11) Å, and R factor = 0.0450. The author has deposited atomic coordinates for this structure 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.
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34. Details of the biological studies along with acyl-CoA:cholesterol acyltransferase (ACAT) inhibitory activities of various pyrone derivatives will be reported in separate manuscripts in due course.