α-Carbonyl Radical Cyclization Approach toward Angular Triquinanes: Total Synthesis of Enantiomerically Pure (-)-5-Oxosilphiperfol-6-ene

Journal of Organic Chemistry

Volumn 63, Issue 8, 1998, Pages 2699-2704

  Sha, Chin Kang ^a   Santhosh, K C ^a   Lib, Shin Hong ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000286841     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9723570     Document Type: Article

References (33)

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3. (a) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry. Reactivity and Structure Concepts in Organic Chemistry; Springer-Verlag: Berlin, 1989; Vol 26.
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6. (d) Hudlicky, T. In Studies in Natural Products Chemistry; Rahman, A., Ed.; Stereoselective Synthesis (part B); Elsevier: New York, 1989; Vol 3, pp 3-72.
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8. For radical cyclization approaches to triquinanes, see: (a) Beckwith, A. L. J.; Roberts, D. H.; Schiesser, C. H.; Wallner, A. Tetrahedron Lett. 1985, 26, 3349. (b) Curran, D. P.; Kuo, S.-C. Tetrahedron 1987, 43, 5653. (c) Curran, D. P.; Rakiewicz, D. M. J. Am. Chem. Soc. 1985, 107, 1448. Winkler, J. D.; Sridar, V. J. Am. Chem. Soc. 1986, 108, 1708. (e) Meyers, A. I.; Lefker, B. A. Tetrahedron 1987, 43, 5663. (f) Little, R. D.; Muller, G. W.; Venegas, M. G.; Carrol. G. L.; Bukhari, A.; Patton, L.; Stone, K. Tetrahedron 1981, 37, 4371. (g) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (h) Hollingworth, G. J.; Pattenden, G.; Schultz, D. J.; Aust. J. Chem. 1995, 48, 381.
9. For radical cyclization approaches to triquinanes, see: (a) Beckwith, A. L. J.; Roberts, D. H.; Schiesser, C. H.; Wallner, A. Tetrahedron Lett. 1985, 26, 3349. (b) Curran, D. P.; Kuo, S.-C. Tetrahedron 1987, 43, 5653. (c) Curran, D. P.; Rakiewicz, D. M. J. Am. Chem. Soc. 1985, 107, 1448. Winkler, J. D.; Sridar, V. J. Am. Chem. Soc. 1986, 108, 1708. (e) Meyers, A. I.; Lefker, B. A. Tetrahedron 1987, 43, 5663. (f) Little, R. D.; Muller, G. W.; Venegas, M. G.; Carrol. G. L.; Bukhari, A.; Patton, L.; Stone, K. Tetrahedron 1981, 37, 4371. (g) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (h) Hollingworth, G. J.; Pattenden, G.; Schultz, D. J.; Aust. J. Chem. 1995, 48, 381.
10. For radical cyclization approaches to triquinanes, see: (a) Beckwith, A. L. J.; Roberts, D. H.; Schiesser, C. H.; Wallner, A. Tetrahedron Lett. 1985, 26, 3349. (b) Curran, D. P.; Kuo, S.-C. Tetrahedron 1987, 43, 5653. (c) Curran, D. P.; Rakiewicz, D. M. J. Am. Chem. Soc. 1985, 107, 1448. Winkler, J. D.; Sridar, V. J. Am. Chem. Soc. 1986, 108, 1708. (e) Meyers, A. I.; Lefker, B. A. Tetrahedron 1987, 43, 5663. (f) Little, R. D.; Muller, G. W.; Venegas, M. G.; Carrol. G. L.; Bukhari, A.; Patton, L.; Stone, K. Tetrahedron 1981, 37, 4371. (g) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (h) Hollingworth, G. J.; Pattenden, G.; Schultz, D. J.; Aust. J. Chem. 1995, 48, 381.
11. For radical cyclization approaches to triquinanes, see: (a) Beckwith, A. L. J.; Roberts, D. H.; Schiesser, C. H.; Wallner, A. Tetrahedron Lett. 1985, 26, 3349. (b) Curran, D. P.; Kuo, S.-C. Tetrahedron 1987, 43, 5653. (c) Curran, D. P.; Rakiewicz, D. M. J. Am. Chem. Soc. 1985, 107, 1448. Winkler, J. D.; Sridar, V. J. Am. Chem. Soc. 1986, 108, 1708. (e) Meyers, A. I.; Lefker, B. A. Tetrahedron 1987, 43, 5663. (f) Little, R. D.; Muller, G. W.; Venegas, M. G.; Carrol. G. L.; Bukhari, A.; Patton, L.; Stone, K. Tetrahedron 1981, 37, 4371. (g) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (h) Hollingworth, G. J.; Pattenden, G.; Schultz, D. J.; Aust. J. Chem. 1995, 48, 381.
12. For radical cyclization approaches to triquinanes, see: (a) Beckwith, A. L. J.; Roberts, D. H.; Schiesser, C. H.; Wallner, A. Tetrahedron Lett. 1985, 26, 3349. (b) Curran, D. P.; Kuo, S.-C. Tetrahedron 1987, 43, 5653. (c) Curran, D. P.; Rakiewicz, D. M. J. Am. Chem. Soc. 1985, 107, 1448. Winkler, J. D.; Sridar, V. J. Am. Chem. Soc. 1986, 108, 1708. (e) Meyers, A. I.; Lefker, B. A. Tetrahedron 1987, 43, 5663. (f) Little, R. D.; Muller, G. W.; Venegas, M. G.; Carrol. G. L.; Bukhari, A.; Patton, L.; Stone, K. Tetrahedron 1981, 37, 4371. (g) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (h) Hollingworth, G. J.; Pattenden, G.; Schultz, D. J.; Aust. J. Chem. 1995, 48, 381.
13. For radical cyclization approaches to triquinanes, see: (a) Beckwith, A. L. J.; Roberts, D. H.; Schiesser, C. H.; Wallner, A. Tetrahedron Lett. 1985, 26, 3349. (b) Curran, D. P.; Kuo, S.-C. Tetrahedron 1987, 43, 5653. (c) Curran, D. P.; Rakiewicz, D. M. J. Am. Chem. Soc. 1985, 107, 1448. Winkler, J. D.; Sridar, V. J. Am. Chem. Soc. 1986, 108, 1708. (e) Meyers, A. I.; Lefker, B. A. Tetrahedron 1987, 43, 5663. (f) Little, R. D.; Muller, G. W.; Venegas, M. G.; Carrol. G. L.; Bukhari, A.; Patton, L.; Stone, K. Tetrahedron 1981, 37, 4371. (g) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (h) Hollingworth, G. J.; Pattenden, G.; Schultz, D. J.; Aust. J. Chem. 1995, 48, 381.
14. For radical cyclization approaches to triquinanes, see: (a) Beckwith, A. L. J.; Roberts, D. H.; Schiesser, C. H.; Wallner, A. Tetrahedron Lett. 1985, 26, 3349. (b) Curran, D. P.; Kuo, S.-C. Tetrahedron 1987, 43, 5653. (c) Curran, D. P.; Rakiewicz, D. M. J. Am. Chem. Soc. 1985, 107, 1448. Winkler, J. D.; Sridar, V. J. Am. Chem. Soc. 1986, 108, 1708. (e) Meyers, A. I.; Lefker, B. A. Tetrahedron 1987, 43, 5663. (f) Little, R. D.; Muller, G. W.; Venegas, M. G.; Carrol. G. L.; Bukhari, A.; Patton, L.; Stone, K. Tetrahedron 1981, 37, 4371. (g) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (h) Hollingworth, G. J.; Pattenden, G.; Schultz, D. J.; Aust. J. Chem. 1995, 48, 381.
15. For radical cyclization approaches to triquinanes, see: (a) Beckwith, A. L. J.; Roberts, D. H.; Schiesser, C. H.; Wallner, A. Tetrahedron Lett. 1985, 26, 3349. (b) Curran, D. P.; Kuo, S.-C. Tetrahedron 1987, 43, 5653. (c) Curran, D. P.; Rakiewicz, D. M. J. Am. Chem. Soc. 1985, 107, 1448. Winkler, J. D.; Sridar, V. J. Am. Chem. Soc. 1986, 108, 1708. (e) Meyers, A. I.; Lefker, B. A. Tetrahedron 1987, 43, 5663. (f) Little, R. D.; Muller, G. W.; Venegas, M. G.; Carrol. G. L.; Bukhari, A.; Patton, L.; Stone, K. Tetrahedron 1981, 37, 4371. (g) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (h) Hollingworth, G. J.; Pattenden, G.; Schultz, D. J.; Aust. J. Chem. 1995, 48, 381.
16. Earlier reports on the total synthesis of 1: (a) Demuth, M.; Hinsken, W. Helv. Chim. Acta 1988, 71, 569. (b) Kakiuchi, K.; Ue, M.; Tsukahara, H.; Shimisu, T.; Miyao, T.; Tobe, Y.; Odaira, Y.; Yasuda, M.; Shima, K. J. Am. Chem. Soc. 1989, 111, 3707. For total synthesis of the closely related natural product silphiperfol-6-ene see: ref 2b and Paquette, L. A.; Roberts, R. A.; Drtina, G. J. J. Am. Chem. Soc. 1984, 106, 6690. Curran, D. P.; Kuo, S.-C. J. Am. Chem. Soc. 1986, 108, 1106. (e) Dickson, J. K., Jr.; Fraser-Reid, B. J. Chem. Soc. Chem. Commun. 1990, 1440. (f) Vo, N. H.; Snider, B. B. J. Org. Chem. 1994, 59, 5419. (g) Wender, P. A.; Singh, S. K. Tetrahedron Lett. 1985, 26, 5987. (h) Wender, P. A.; Ternansky, R.; deLong, M.; Singh, S.; Olivero, A.; Rice, K. Pure Appl. Chem. 1990, 62, 1597. Demuth, M.; Hinsken, W. Angew. Chem., Int. Ed., Engl. 1985, 24, 973.
17. Earlier reports on the total synthesis of 1: (a) Demuth, M.; Hinsken, W. Helv. Chim. Acta 1988, 71, 569. (b) Kakiuchi, K.; Ue, M.; Tsukahara, H.; Shimisu, T.; Miyao, T.; Tobe, Y.; Odaira, Y.; Yasuda, M.; Shima, K. J. Am. Chem. Soc. 1989, 111, 3707. For total synthesis of the closely related natural product silphiperfol-6-ene see: ref 2b and Paquette, L. A.; Roberts, R. A.; Drtina, G. J. J. Am. Chem. Soc. 1984, 106, 6690. Curran, D. P.; Kuo, S.-C. J. Am. Chem. Soc. 1986, 108, 1106. (e) Dickson, J. K., Jr.; Fraser-Reid, B. J. Chem. Soc. Chem. Commun. 1990, 1440. (f) Vo, N. H.; Snider, B. B. J. Org. Chem. 1994, 59, 5419. (g) Wender, P. A.; Singh, S. K. Tetrahedron Lett. 1985, 26, 5987. (h) Wender, P. A.; Ternansky, R.; deLong, M.; Singh, S.; Olivero, A.; Rice, K. Pure Appl. Chem. 1990, 62, 1597. Demuth, M.; Hinsken, W. Angew. Chem., Int. Ed., Engl. 1985, 24, 973.
18. Earlier reports on the total synthesis of 1: (a) Demuth, M.; Hinsken, W. Helv. Chim. Acta 1988, 71, 569. (b) Kakiuchi, K.; Ue, M.; Tsukahara, H.; Shimisu, T.; Miyao, T.; Tobe, Y.; Odaira, Y.; Yasuda, M.; Shima, K. J. Am. Chem. Soc. 1989, 111, 3707. For total synthesis of the closely related natural product silphiperfol-6-ene see: ref 2b and Paquette, L. A.; Roberts, R. A.; Drtina, G. J. J. Am. Chem. Soc. 1984, 106, 6690. Curran, D. P.; Kuo, S.-C. J. Am. Chem. Soc. 1986, 108, 1106. (e) Dickson, J. K., Jr.; Fraser-Reid, B. J. Chem. Soc. Chem. Commun. 1990, 1440. (f) Vo, N. H.; Snider, B. B. J. Org. Chem. 1994, 59, 5419. (g) Wender, P. A.; Singh, S. K. Tetrahedron Lett. 1985, 26, 5987. (h) Wender, P. A.; Ternansky, R.; deLong, M.; Singh, S.; Olivero, A.; Rice, K. Pure Appl. Chem. 1990, 62, 1597. Demuth, M.; Hinsken, W. Angew. Chem., Int. Ed., Engl. 1985, 24, 973.
19. Earlier reports on the total synthesis of 1: (a) Demuth, M.; Hinsken, W. Helv. Chim. Acta 1988, 71, 569. (b) Kakiuchi, K.; Ue, M.; Tsukahara, H.; Shimisu, T.; Miyao, T.; Tobe, Y.; Odaira, Y.; Yasuda, M.; Shima, K. J. Am. Chem. Soc. 1989, 111, 3707. For total synthesis of the closely related natural product silphiperfol-6-ene see: ref 2b and Paquette, L. A.; Roberts, R. A.; Drtina, G. J. J. Am. Chem. Soc. 1984, 106, 6690. Curran, D. P.; Kuo, S.-C. J. Am. Chem. Soc. 1986, 108, 1106. (e) Dickson, J. K., Jr.; Fraser-Reid, B. J. Chem. Soc. Chem. Commun. 1990, 1440. (f) Vo, N. H.; Snider, B. B. J. Org. Chem. 1994, 59, 5419. (g) Wender, P. A.; Singh, S. K. Tetrahedron Lett. 1985, 26, 5987. (h) Wender, P. A.; Ternansky, R.; deLong, M.; Singh, S.; Olivero, A.; Rice, K. Pure Appl. Chem. 1990, 62, 1597. Demuth, M.; Hinsken, W. Angew. Chem., Int. Ed., Engl. 1985, 24, 973.
20. Earlier reports on the total synthesis of 1: (a) Demuth, M.; Hinsken, W. Helv. Chim. Acta 1988, 71, 569. (b) Kakiuchi, K.; Ue, M.; Tsukahara, H.; Shimisu, T.; Miyao, T.; Tobe, Y.; Odaira, Y.; Yasuda, M.; Shima, K. J. Am. Chem. Soc. 1989, 111, 3707. For total synthesis of the closely related natural product silphiperfol-6-ene see: ref 2b and Paquette, L. A.; Roberts, R. A.; Drtina, G. J. J. Am. Chem. Soc. 1984, 106, 6690. Curran, D. P.; Kuo, S.-C. J. Am. Chem. Soc. 1986, 108, 1106. (e) Dickson, J. K., Jr.; Fraser-Reid, B. J. Chem. Soc. Chem. Commun. 1990, 1440. (f) Vo, N. H.; Snider, B. B. J. Org. Chem. 1994, 59, 5419. (g) Wender, P. A.; Singh, S. K. Tetrahedron Lett. 1985, 26, 5987. (h) Wender, P. A.; Ternansky, R.; deLong, M.; Singh, S.; Olivero, A.; Rice, K. Pure Appl. Chem. 1990, 62, 1597. Demuth, M.; Hinsken, W. Angew. Chem., Int. Ed., Engl. 1985, 24, 973.
21. Earlier reports on the total synthesis of 1: (a) Demuth, M.; Hinsken, W. Helv. Chim. Acta 1988, 71, 569. (b) Kakiuchi, K.; Ue, M.; Tsukahara, H.; Shimisu, T.; Miyao, T.; Tobe, Y.; Odaira, Y.; Yasuda, M.; Shima, K. J. Am. Chem. Soc. 1989, 111, 3707. For total synthesis of the closely related natural product silphiperfol-6-ene see: ref 2b and Paquette, L. A.; Roberts, R. A.; Drtina, G. J. J. Am. Chem. Soc. 1984, 106, 6690. Curran, D. P.; Kuo, S.-C. J. Am. Chem. Soc. 1986, 108, 1106. (e) Dickson, J. K., Jr.; Fraser-Reid, B. J. Chem. Soc. Chem. Commun. 1990, 1440. (f) Vo, N. H.; Snider, B. B. J. Org. Chem. 1994, 59, 5419. (g) Wender, P. A.; Singh, S. K. Tetrahedron Lett. 1985, 26, 5987. (h) Wender, P. A.; Ternansky, R.; deLong, M.; Singh, S.; Olivero, A.; Rice, K. Pure Appl. Chem. 1990, 62, 1597. Demuth, M.; Hinsken, W. Angew. Chem., Int. Ed., Engl. 1985, 24, 973.
22. Earlier reports on the total synthesis of 1: (a) Demuth, M.; Hinsken, W. Helv. Chim. Acta 1988, 71, 569. (b) Kakiuchi, K.; Ue, M.; Tsukahara, H.; Shimisu, T.; Miyao, T.; Tobe, Y.; Odaira, Y.; Yasuda, M.; Shima, K. J. Am. Chem. Soc. 1989, 111, 3707. For total synthesis of the closely related natural product silphiperfol-6-ene see: ref 2b and Paquette, L. A.; Roberts, R. A.; Drtina, G. J. J. Am. Chem. Soc. 1984, 106, 6690. Curran, D. P.; Kuo, S.-C. J. Am. Chem. Soc. 1986, 108, 1106. (e) Dickson, J. K., Jr.; Fraser-Reid, B. J. Chem. Soc. Chem. Commun. 1990, 1440. (f) Vo, N. H.; Snider, B. B. J. Org. Chem. 1994, 59, 5419. (g) Wender, P. A.; Singh, S. K. Tetrahedron Lett. 1985, 26, 5987. (h) Wender, P. A.; Ternansky, R.; deLong, M.; Singh, S.; Olivero, A.; Rice, K. Pure Appl. Chem. 1990, 62, 1597. Demuth, M.; Hinsken, W. Angew. Chem., Int. Ed., Engl. 1985, 24, 973.
23. Earlier reports on the total synthesis of 1: (a) Demuth, M.; Hinsken, W. Helv. Chim. Acta 1988, 71, 569. (b) Kakiuchi, K.; Ue, M.; Tsukahara, H.; Shimisu, T.; Miyao, T.; Tobe, Y.; Odaira, Y.; Yasuda, M.; Shima, K. J. Am. Chem. Soc. 1989, 111, 3707. For total synthesis of the closely related natural product silphiperfol-6-ene see: ref 2b and Paquette, L. A.; Roberts, R. A.; Drtina, G. J. J. Am. Chem. Soc. 1984, 106, 6690. Curran, D. P.; Kuo, S.-C. J. Am. Chem. Soc. 1986, 108, 1106. (e) Dickson, J. K., Jr.; Fraser-Reid, B. J. Chem. Soc. Chem. Commun. 1990, 1440. (f) Vo, N. H.; Snider, B. B. J. Org. Chem. 1994, 59, 5419. (g) Wender, P. A.; Singh, S. K. Tetrahedron Lett. 1985, 26, 5987. (h) Wender, P. A.; Ternansky, R.; deLong, M.; Singh, S.; Olivero, A.; Rice, K. Pure Appl. Chem. 1990, 62, 1597. Demuth, M.; Hinsken, W. Angew. Chem., Int. Ed., Engl. 1985, 24, 973.
24. Earlier reports on the total synthesis of 1: (a) Demuth, M.; Hinsken, W. Helv. Chim. Acta 1988, 71, 569. (b) Kakiuchi, K.; Ue, M.; Tsukahara, H.; Shimisu, T.; Miyao, T.; Tobe, Y.; Odaira, Y.; Yasuda, M.; Shima, K. J. Am. Chem. Soc. 1989, 111, 3707. For total synthesis of the closely related natural product silphiperfol-6-ene see: ref 2b and Paquette, L. A.; Roberts, R. A.; Drtina, G. J. J. Am. Chem. Soc. 1984, 106, 6690. Curran, D. P.; Kuo, S.-C. J. Am. Chem. Soc. 1986, 108, 1106. (e) Dickson, J. K., Jr.; Fraser-Reid, B. J. Chem. Soc. Chem. Commun. 1990, 1440. (f) Vo, N. H.; Snider, B. B. J. Org. Chem. 1994, 59, 5419. (g) Wender, P. A.; Singh, S. K. Tetrahedron Lett. 1985, 26, 5987. (h) Wender, P. A.; Ternansky, R.; deLong, M.; Singh, S.; Olivero, A.; Rice, K. Pure Appl. Chem. 1990, 62, 1597. Demuth, M.; Hinsken, W. Angew. Chem., Int. Ed., Engl. 1985, 24, 973.
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33. 13C NMR, IR, and MS of 1 are in good agreement with those spectra received from Professor M. Demuth.