Preparation of γ,δ-unsaturated β-ketophosphonates from tertiary α-allenic alcohols. The synthesis of (±)-(E)-α-atlantone

Journal of Organic Chemistry

Volumn 61, Issue 20, 1996, Pages 7202-7206

  Friesen, Richard W ^a   Blouin, Marc ^a  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA ATLANTONE; TERPENOID; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029843389     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960894z     Document Type: Article

References (80)

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16. For reviews, see: (a) Denmark, S. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 751-784. (b) Santelli-Rouvier, C.; Santelli, M. Synthesis 1983, 429. For some recent examples and applications, see: (c) Kang, K.-T.; Kim, S. S.; Lee, J. C.; U, J. S. Tetrahedron Lett. 1992, 33, 3495. (d) Frank-Neumann, M.; Miesch, M.; Gross, L. Tetrahedron Lett. 1992, 33, 3879. (e) Paquette, L. A.; Kang, H.-J. J. Am. Chem. Soc. 1991, 113, 2610. (f) Andrews, J. F. P.; Began, A. C. Tetrahedron Lett. 1991, 32, 7731. (g) Yamazaki, S.; Mizuno, W.; Yamabe, S. J. Chem. Soc., Perkin Trans. 1 1991, 1555. (h) See also refs 2a,b.
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18. For some selected examples of other reactions of cross-conjugated ketones, see: (a) Krein, E. B.; Aizenshtat, Z. J. Org. Chem. 1993, 58, 6103. (b) Chiacchio, U.; Corsaro, A.; Rescifina, A.; Testa, M. G.; Purrello, G. Heterocycles 1993, 36, 223. (c) Nakamura, E.; Kubota, K.; Isaka, M. J. Org. Chem. 1992, 57, 5809. (d) Hitchcock, S. A.; Pattenden, G. Tetrahedron Lett. 1992, 33, 4843. (e) Grigg, R.; Kenhewell, P.; Savic, V.; Sridharan, V. Tetrahedron 1992, 48, 10423. (f) Yamaguchi, M.; Hayashi, A.; Hirama, M. Chem. Lett. 1992, 2479. (g) Diaz, E.; Barrios, H.; Toscano, R. A.; Yuste, F.; Reynolds, W. F.; Aguilera, J. L.; Caballero, E. J. Heterocycl. Chem. 1992, 29, 1325. (h) Hagiwara, H.; Okano, A.; Uda, H. J. Chem. Soc., Perkin Trans. 1 1990, 2109. (i) Richter, F.; Otto, H.-H. Liebigs Ann. Chem. 1990, 7. (j) Richter, F.; Otto, H.-H. Tetrahedron Lett. 1985, 26, 4351. (k) Britten-Kelly, M.; Willis, B. J. Synthesis 1980, 27.
19. For some selected examples of other reactions of cross-conjugated ketones, see: (a) Krein, E. B.; Aizenshtat, Z. J. Org. Chem. 1993, 58, 6103. (b) Chiacchio, U.; Corsaro, A.; Rescifina, A.; Testa, M. G.; Purrello, G. Heterocycles 1993, 36, 223. (c) Nakamura, E.; Kubota, K.; Isaka, M. J. Org. Chem. 1992, 57, 5809. (d) Hitchcock, S. A.; Pattenden, G. Tetrahedron Lett. 1992, 33, 4843. (e) Grigg, R.; Kenhewell, P.; Savic, V.; Sridharan, V. Tetrahedron 1992, 48, 10423. (f) Yamaguchi, M.; Hayashi, A.; Hirama, M. Chem. Lett. 1992, 2479. (g) Diaz, E.; Barrios, H.; Toscano, R. A.; Yuste, F.; Reynolds, W. F.; Aguilera, J. L.; Caballero, E. J. Heterocycl. Chem. 1992, 29, 1325. (h) Hagiwara, H.; Okano, A.; Uda, H. J. Chem. Soc., Perkin Trans. 1 1990, 2109. (i) Richter, F.; Otto, H.-H. Liebigs Ann. Chem. 1990, 7. (j) Richter, F.; Otto, H.-H. Tetrahedron Lett. 1985, 26, 4351. (k) Britten-Kelly, M.; Willis, B. J. Synthesis 1980, 27.
20. For some selected examples of other reactions of cross-conjugated ketones, see: (a) Krein, E. B.; Aizenshtat, Z. J. Org. Chem. 1993, 58, 6103. (b) Chiacchio, U.; Corsaro, A.; Rescifina, A.; Testa, M. G.; Purrello, G. Heterocycles 1993, 36, 223. (c) Nakamura, E.; Kubota, K.; Isaka, M. J. Org. Chem. 1992, 57, 5809. (d) Hitchcock, S. A.; Pattenden, G. Tetrahedron Lett. 1992, 33, 4843. (e) Grigg, R.; Kenhewell, P.; Savic, V.; Sridharan, V. Tetrahedron 1992, 48, 10423. (f) Yamaguchi, M.; Hayashi, A.; Hirama, M. Chem. Lett. 1992, 2479. (g) Diaz, E.; Barrios, H.; Toscano, R. A.; Yuste, F.; Reynolds, W. F.; Aguilera, J. L.; Caballero, E. J. Heterocycl. Chem. 1992, 29, 1325. (h) Hagiwara, H.; Okano, A.; Uda, H. J. Chem. Soc., Perkin Trans. 1 1990, 2109. (i) Richter, F.; Otto, H.-H. Liebigs Ann. Chem. 1990, 7. (j) Richter, F.; Otto, H.-H. Tetrahedron Lett. 1985, 26, 4351. (k) Britten-Kelly, M.; Willis, B. J. Synthesis 1980, 27.
21. For some selected examples of other reactions of cross-conjugated ketones, see: (a) Krein, E. B.; Aizenshtat, Z. J. Org. Chem. 1993, 58, 6103. (b) Chiacchio, U.; Corsaro, A.; Rescifina, A.; Testa, M. G.; Purrello, G. Heterocycles 1993, 36, 223. (c) Nakamura, E.; Kubota, K.; Isaka, M. J. Org. Chem. 1992, 57, 5809. (d) Hitchcock, S. A.; Pattenden, G. Tetrahedron Lett. 1992, 33, 4843. (e) Grigg, R.; Kenhewell, P.; Savic, V.; Sridharan, V. Tetrahedron 1992, 48, 10423. (f) Yamaguchi, M.; Hayashi, A.; Hirama, M. Chem. Lett. 1992, 2479. (g) Diaz, E.; Barrios, H.; Toscano, R. A.; Yuste, F.; Reynolds, W. F.; Aguilera, J. L.; Caballero, E. J. Heterocycl. Chem. 1992, 29, 1325. (h) Hagiwara, H.; Okano, A.; Uda, H. J. Chem. Soc., Perkin Trans. 1 1990, 2109. (i) Richter, F.; Otto, H.-H. Liebigs Ann. Chem. 1990, 7. (j) Richter, F.; Otto, H.-H. Tetrahedron Lett. 1985, 26, 4351. (k) Britten-Kelly, M.; Willis, B. J. Synthesis 1980, 27.
22. For some selected examples of other reactions of cross-conjugated ketones, see: (a) Krein, E. B.; Aizenshtat, Z. J. Org. Chem. 1993, 58, 6103. (b) Chiacchio, U.; Corsaro, A.; Rescifina, A.; Testa, M. G.; Purrello, G. Heterocycles 1993, 36, 223. (c) Nakamura, E.; Kubota, K.; Isaka, M. J. Org. Chem. 1992, 57, 5809. (d) Hitchcock, S. A.; Pattenden, G. Tetrahedron Lett. 1992, 33, 4843. (e) Grigg, R.; Kenhewell, P.; Savic, V.; Sridharan, V. Tetrahedron 1992, 48, 10423. (f) Yamaguchi, M.; Hayashi, A.; Hirama, M. Chem. Lett. 1992, 2479. (g) Diaz, E.; Barrios, H.; Toscano, R. A.; Yuste, F.; Reynolds, W. F.; Aguilera, J. L.; Caballero, E. J. Heterocycl. Chem. 1992, 29, 1325. (h) Hagiwara, H.; Okano, A.; Uda, H. J. Chem. Soc., Perkin Trans. 1 1990, 2109. (i) Richter, F.; Otto, H.-H. Liebigs Ann. Chem. 1990, 7. (j) Richter, F.; Otto, H.-H. Tetrahedron Lett. 1985, 26, 4351. (k) Britten-Kelly, M.; Willis, B. J. Synthesis 1980, 27.
23. For some selected examples of other reactions of cross-conjugated ketones, see: (a) Krein, E. B.; Aizenshtat, Z. J. Org. Chem. 1993, 58, 6103. (b) Chiacchio, U.; Corsaro, A.; Rescifina, A.; Testa, M. G.; Purrello, G. Heterocycles 1993, 36, 223. (c) Nakamura, E.; Kubota, K.; Isaka, M. J. Org. Chem. 1992, 57, 5809. (d) Hitchcock, S. A.; Pattenden, G. Tetrahedron Lett. 1992, 33, 4843. (e) Grigg, R.; Kenhewell, P.; Savic, V.; Sridharan, V. Tetrahedron 1992, 48, 10423. (f) Yamaguchi, M.; Hayashi, A.; Hirama, M. Chem. Lett. 1992, 2479. (g) Diaz, E.; Barrios, H.; Toscano, R. A.; Yuste, F.; Reynolds, W. F.; Aguilera, J. L.; Caballero, E. J. Heterocycl. Chem. 1992, 29, 1325. (h) Hagiwara, H.; Okano, A.; Uda, H. J. Chem. Soc., Perkin Trans. 1 1990, 2109. (i) Richter, F.; Otto, H.-H. Liebigs Ann. Chem. 1990, 7. (j) Richter, F.; Otto, H.-H. Tetrahedron Lett. 1985, 26, 4351. (k) Britten-Kelly, M.; Willis, B. J. Synthesis 1980, 27.
24. For some selected examples of other reactions of cross-conjugated ketones, see: (a) Krein, E. B.; Aizenshtat, Z. J. Org. Chem. 1993, 58, 6103. (b) Chiacchio, U.; Corsaro, A.; Rescifina, A.; Testa, M. G.; Purrello, G. Heterocycles 1993, 36, 223. (c) Nakamura, E.; Kubota, K.; Isaka, M. J. Org. Chem. 1992, 57, 5809. (d) Hitchcock, S. A.; Pattenden, G. Tetrahedron Lett. 1992, 33, 4843. (e) Grigg, R.; Kenhewell, P.; Savic, V.; Sridharan, V. Tetrahedron 1992, 48, 10423. (f) Yamaguchi, M.; Hayashi, A.; Hirama, M. Chem. Lett. 1992, 2479. (g) Diaz, E.; Barrios, H.; Toscano, R. A.; Yuste, F.; Reynolds, W. F.; Aguilera, J. L.; Caballero, E. J. Heterocycl. Chem. 1992, 29, 1325. (h) Hagiwara, H.; Okano, A.; Uda, H. J. Chem. Soc., Perkin Trans. 1 1990, 2109. (i) Richter, F.; Otto, H.-H. Liebigs Ann. Chem. 1990, 7. (j) Richter, F.; Otto, H.-H. Tetrahedron Lett. 1985, 26, 4351. (k) Britten-Kelly, M.; Willis, B. J. Synthesis 1980, 27.
25. For some selected examples of other reactions of cross-conjugated ketones, see: (a) Krein, E. B.; Aizenshtat, Z. J. Org. Chem. 1993, 58, 6103. (b) Chiacchio, U.; Corsaro, A.; Rescifina, A.; Testa, M. G.; Purrello, G. Heterocycles 1993, 36, 223. (c) Nakamura, E.; Kubota, K.; Isaka, M. J. Org. Chem. 1992, 57, 5809. (d) Hitchcock, S. A.; Pattenden, G. Tetrahedron Lett. 1992, 33, 4843. (e) Grigg, R.; Kenhewell, P.; Savic, V.; Sridharan, V. Tetrahedron 1992, 48, 10423. (f) Yamaguchi, M.; Hayashi, A.; Hirama, M. Chem. Lett. 1992, 2479. (g) Diaz, E.; Barrios, H.; Toscano, R. A.; Yuste, F.; Reynolds, W. F.; Aguilera, J. L.; Caballero, E. J. Heterocycl. Chem. 1992, 29, 1325. (h) Hagiwara, H.; Okano, A.; Uda, H. J. Chem. Soc., Perkin Trans. 1 1990, 2109. (i) Richter, F.; Otto, H.-H. Liebigs Ann. Chem. 1990, 7. (j) Richter, F.; Otto, H.-H. Tetrahedron Lett. 1985, 26, 4351. (k) Britten-Kelly, M.; Willis, B. J. Synthesis 1980, 27.
26. For some selected examples of other reactions of cross-conjugated ketones, see: (a) Krein, E. B.; Aizenshtat, Z. J. Org. Chem. 1993, 58, 6103. (b) Chiacchio, U.; Corsaro, A.; Rescifina, A.; Testa, M. G.; Purrello, G. Heterocycles 1993, 36, 223. (c) Nakamura, E.; Kubota, K.; Isaka, M. J. Org. Chem. 1992, 57, 5809. (d) Hitchcock, S. A.; Pattenden, G. Tetrahedron Lett. 1992, 33, 4843. (e) Grigg, R.; Kenhewell, P.; Savic, V.; Sridharan, V. Tetrahedron 1992, 48, 10423. (f) Yamaguchi, M.; Hayashi, A.; Hirama, M. Chem. Lett. 1992, 2479. (g) Diaz, E.; Barrios, H.; Toscano, R. A.; Yuste, F.; Reynolds, W. F.; Aguilera, J. L.; Caballero, E. J. Heterocycl. Chem. 1992, 29, 1325. (h) Hagiwara, H.; Okano, A.; Uda, H. J. Chem. Soc., Perkin Trans. 1 1990, 2109. (i) Richter, F.; Otto, H.-H. Liebigs Ann. Chem. 1990, 7. (j) Richter, F.; Otto, H.-H. Tetrahedron Lett. 1985, 26, 4351. (k) Britten-Kelly, M.; Willis, B. J. Synthesis 1980, 27.
27. For some selected examples of other reactions of cross-conjugated ketones, see: (a) Krein, E. B.; Aizenshtat, Z. J. Org. Chem. 1993, 58, 6103. (b) Chiacchio, U.; Corsaro, A.; Rescifina, A.; Testa, M. G.; Purrello, G. Heterocycles 1993, 36, 223. (c) Nakamura, E.; Kubota, K.; Isaka, M. J. Org. Chem. 1992, 57, 5809. (d) Hitchcock, S. A.; Pattenden, G. Tetrahedron Lett. 1992, 33, 4843. (e) Grigg, R.; Kenhewell, P.; Savic, V.; Sridharan, V. Tetrahedron 1992, 48, 10423. (f) Yamaguchi, M.; Hayashi, A.; Hirama, M. Chem. Lett. 1992, 2479. (g) Diaz, E.; Barrios, H.; Toscano, R. A.; Yuste, F.; Reynolds, W. F.; Aguilera, J. L.; Caballero, E. J. Heterocycl. Chem. 1992, 29, 1325. (h) Hagiwara, H.; Okano, A.; Uda, H. J. Chem. Soc., Perkin Trans. 1 1990, 2109. (i) Richter, F.; Otto, H.-H. Liebigs Ann. Chem. 1990, 7. (j) Richter, F.; Otto, H.-H. Tetrahedron Lett. 1985, 26, 4351. (k) Britten-Kelly, M.; Willis, B. J. Synthesis 1980, 27.
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50. For reactions of alkylphosphonate anions with α,β-unsaturated carboxylic acid chlorides and/or esters, see: (a) Corey, E. J.; Ohuchida, S.; Hahl, R. J. Am. Chem. Soc. 1984, 106, 3875. (b) Mathey, F.; Savignac, P. Tetrahedron 1978, 34, 649. (c) Aboujaoude, E. E.; Collignon, N.; Teulade, M.-P.; Savignac, P. Phosphorus Sulfur 1985, 25, 57. (d) See also refs 2b-d,f. For other methods of preparation, see: (e) Koh, Y. J.; Oh, D. Y. Tetrahedron Lett. 1993, 34, 2147. (f) Tsuge, O.; Kanemasa, S.; Suga, H.; Nakagawa, N. Bull. Chem. Soc. Jpn. 1987, 60, 2463. (g) Peiffer, G.; Courbis, P. Can. J. Chem. 1974, 52, 2894. (h) See also refs 2e, 7c, and 8. For examples with γ,δ-unsaturation within a carbocycle, see: (i) An, Y.-Z.; An, J. G.; Wiemer, D. F. J. Org. Chem. 1994, 59, 8197 and refs cited therein. (j) Castagnino, E.; D'Auria, M.; De Mico, A.; D'Onofrio, F.; Piancatelli, G. J. Chem. Soc., Chem. Commun. 1987, 907. (k) See also ref 12 and refs cited therein.
51. For reactions of alkylphosphonate anions with α,β-unsaturated carboxylic acid chlorides and/or esters, see: (a) Corey, E. J.; Ohuchida, S.; Hahl, R. J. Am. Chem. Soc. 1984, 106, 3875. (b) Mathey, F.; Savignac, P. Tetrahedron 1978, 34, 649. (c) Aboujaoude, E. E.; Collignon, N.; Teulade, M.-P.; Savignac, P. Phosphorus Sulfur 1985, 25, 57. (d) See also refs 2b-d,f. For other methods of preparation, see: (e) Koh, Y. J.; Oh, D. Y. Tetrahedron Lett. 1993, 34, 2147. (f) Tsuge, O.; Kanemasa, S.; Suga, H.; Nakagawa, N. Bull. Chem. Soc. Jpn. 1987, 60, 2463. (g) Peiffer, G.; Courbis, P. Can. J. Chem. 1974, 52, 2894. (h) See also refs 2e, 7c, and 8. For examples with γ,δ-unsaturation within a carbocycle, see: (i) An, Y.-Z.; An, J. G.; Wiemer, D. F. J. Org. Chem. 1994, 59, 8197 and refs cited therein. (j) Castagnino, E.; D'Auria, M.; De Mico, A.; D'Onofrio, F.; Piancatelli, G. J. Chem. Soc., Chem. Commun. 1987, 907. (k) See also ref 12 and refs cited therein.
52. For reactions of alkylphosphonate anions with α,β-unsaturated carboxylic acid chlorides and/or esters, see: (a) Corey, E. J.; Ohuchida, S.; Hahl, R. J. Am. Chem. Soc. 1984, 106, 3875. (b) Mathey, F.; Savignac, P. Tetrahedron 1978, 34, 649. (c) Aboujaoude, E. E.; Collignon, N.; Teulade, M.-P.; Savignac, P. Phosphorus Sulfur 1985, 25, 57. (d) See also refs 2b-d,f. For other methods of preparation, see: (e) Koh, Y. J.; Oh, D. Y. Tetrahedron Lett. 1993, 34, 2147. (f) Tsuge, O.; Kanemasa, S.; Suga, H.; Nakagawa, N. Bull. Chem. Soc. Jpn. 1987, 60, 2463. (g) Peiffer, G.; Courbis, P. Can. J. Chem. 1974, 52, 2894. (h) See also refs 2e, 7c, and 8. For examples with γ,δ-unsaturation within a carbocycle, see: (i) An, Y.-Z.; An, J. G.; Wiemer, D. F. J. Org. Chem. 1994, 59, 8197 and refs cited therein. (j) Castagnino, E.; D'Auria, M.; De Mico, A.; D'Onofrio, F.; Piancatelli, G. J. Chem. Soc., Chem. Commun. 1987, 907. (k) See also ref 12 and refs cited therein.
53. For reactions of alkylphosphonate anions with α,β-unsaturated carboxylic acid chlorides and/or esters, see: (a) Corey, E. J.; Ohuchida, S.; Hahl, R. J. Am. Chem. Soc. 1984, 106, 3875. (b) Mathey, F.; Savignac, P. Tetrahedron 1978, 34, 649. (c) Aboujaoude, E. E.; Collignon, N.; Teulade, M.-P.; Savignac, P. Phosphorus Sulfur 1985, 25, 57. (d) See also refs 2b-d,f. For other methods of preparation, see: (e) Koh, Y. J.; Oh, D. Y. Tetrahedron Lett. 1993, 34, 2147. (f) Tsuge, O.; Kanemasa, S.; Suga, H.; Nakagawa, N. Bull. Chem. Soc. Jpn. 1987, 60, 2463. (g) Peiffer, G.; Courbis, P. Can. J. Chem. 1974, 52, 2894. (h) See also refs 2e, 7c, and 8. For examples with γ,δ-unsaturation within a carbocycle, see: (i) An, Y.-Z.; An, J. G.; Wiemer, D. F. J. Org. Chem. 1994, 59, 8197 and refs cited therein. (j) Castagnino, E.; D'Auria, M.; De Mico, A.; D'Onofrio, F.; Piancatelli, G. J. Chem. Soc., Chem. Commun. 1987, 907. (k) See also ref 12 and refs cited therein.
54. For reactions of alkylphosphonate anions with α,β-unsaturated carboxylic acid chlorides and/or esters, see: (a) Corey, E. J.; Ohuchida, S.; Hahl, R. J. Am. Chem. Soc. 1984, 106, 3875. (b) Mathey, F.; Savignac, P. Tetrahedron 1978, 34, 649. (c) Aboujaoude, E. E.; Collignon, N.; Teulade, M.-P.; Savignac, P. Phosphorus Sulfur 1985, 25, 57. (d) See also refs 2b-d,f. For other methods of preparation, see: (e) Koh, Y. J.; Oh, D. Y. Tetrahedron Lett. 1993, 34, 2147. (f) Tsuge, O.; Kanemasa, S.; Suga, H.; Nakagawa, N. Bull. Chem. Soc. Jpn. 1987, 60, 2463. (g) Peiffer, G.; Courbis, P. Can. J. Chem. 1974, 52, 2894. (h) See also refs 2e, 7c, and 8. For examples with γ,δ-unsaturation within a carbocycle, see: (i) An, Y.-Z.; An, J. G.; Wiemer, D. F. J. Org. Chem. 1994, 59, 8197 and refs cited therein. (j) Castagnino, E.; D'Auria, M.; De Mico, A.; D'Onofrio, F.; Piancatelli, G. J. Chem. Soc., Chem. Commun. 1987, 907. (k) See also ref 12 and refs cited therein.
55. For reactions of alkylphosphonate anions with α,β-unsaturated carboxylic acid chlorides and/or esters, see: (a) Corey, E. J.; Ohuchida, S.; Hahl, R. J. Am. Chem. Soc. 1984, 106, 3875. (b) Mathey, F.; Savignac, P. Tetrahedron 1978, 34, 649. (c) Aboujaoude, E. E.; Collignon, N.; Teulade, M.-P.; Savignac, P. Phosphorus Sulfur 1985, 25, 57. (d) See also refs 2b-d,f. For other methods of preparation, see: (e) Koh, Y. J.; Oh, D. Y. Tetrahedron Lett. 1993, 34, 2147. (f) Tsuge, O.; Kanemasa, S.; Suga, H.; Nakagawa, N. Bull. Chem. Soc. Jpn. 1987, 60, 2463. (g) Peiffer, G.; Courbis, P. Can. J. Chem. 1974, 52, 2894. (h) See also refs 2e, 7c, and 8. For examples with γ,δ-unsaturation within a carbocycle, see: (i) An, Y.-Z.; An, J. G.; Wiemer, D. F. J. Org. Chem. 1994, 59, 8197 and refs cited therein. (j) Castagnino, E.; D'Auria, M.; De Mico, A.; D'Onofrio, F.; Piancatelli, G. J. Chem. Soc., Chem. Commun. 1987, 907. (k) See also ref 12 and refs cited therein.
56. For reactions of alkylphosphonate anions with α,β-unsaturated carboxylic acid chlorides and/or esters, see: (a) Corey, E. J.; Ohuchida, S.; Hahl, R. J. Am. Chem. Soc. 1984, 106, 3875. (b) Mathey, F.; Savignac, P. Tetrahedron 1978, 34, 649. (c) Aboujaoude, E. E.; Collignon, N.; Teulade, M.-P.; Savignac, P. Phosphorus Sulfur 1985, 25, 57. (d) See also refs 2b-d,f. For other methods of preparation, see: (e) Koh, Y. J.; Oh, D. Y. Tetrahedron Lett. 1993, 34, 2147. (f) Tsuge, O.; Kanemasa, S.; Suga, H.; Nakagawa, N. Bull. Chem. Soc. Jpn. 1987, 60, 2463. (g) Peiffer, G.; Courbis, P. Can. J. Chem. 1974, 52, 2894. (h) See also refs 2e, 7c, and 8. For examples with γ,δ-unsaturation within a carbocycle, see: (i) An, Y.-Z.; An, J. G.; Wiemer, D. F. J. Org. Chem. 1994, 59, 8197 and refs cited therein. (j) Castagnino, E.; D'Auria, M.; De Mico, A.; D'Onofrio, F.; Piancatelli, G. J. Chem. Soc., Chem. Commun. 1987, 907. (k) See also ref 12 and refs cited therein.
57. For reactions of alkylphosphonate anions with α,β-unsaturated carboxylic acid chlorides and/or esters, see: (a) Corey, E. J.; Ohuchida, S.; Hahl, R. J. Am. Chem. Soc. 1984, 106, 3875. (b) Mathey, F.; Savignac, P. Tetrahedron 1978, 34, 649. (c) Aboujaoude, E. E.; Collignon, N.; Teulade, M.-P.; Savignac, P. Phosphorus Sulfur 1985, 25, 57. (d) See also refs 2b-d,f. For other methods of preparation, see: (e) Koh, Y. J.; Oh, D. Y. Tetrahedron Lett. 1993, 34, 2147. (f) Tsuge, O.; Kanemasa, S.; Suga, H.; Nakagawa, N. Bull. Chem. Soc. Jpn. 1987, 60, 2463. (g) Peiffer, G.; Courbis, P. Can. J. Chem. 1974, 52, 2894. (h) See also refs 2e, 7c, and 8. For examples with γ,δ-unsaturation within a carbocycle, see: (i) An, Y.-Z.; An, J. G.; Wiemer, D. F. J. Org. Chem. 1994, 59, 8197 and refs cited therein. (j) Castagnino, E.; D'Auria, M.; De Mico, A.; D'Onofrio, F.; Piancatelli, G. J. Chem. Soc., Chem. Commun. 1987, 907. (k) See also ref 12 and refs cited therein.
58. For reactions of alkylphosphonate anions with α,β-unsaturated carboxylic acid chlorides and/or esters, see: (a) Corey, E. J.; Ohuchida, S.; Hahl, R. J. Am. Chem. Soc. 1984, 106, 3875. (b) Mathey, F.; Savignac, P. Tetrahedron 1978, 34, 649. (c) Aboujaoude, E. E.; Collignon, N.; Teulade, M.-P.; Savignac, P. Phosphorus Sulfur 1985, 25, 57. (d) See also refs 2b-d,f. For other methods of preparation, see: (e) Koh, Y. J.; Oh, D. Y. Tetrahedron Lett. 1993, 34, 2147. (f) Tsuge, O.; Kanemasa, S.; Suga, H.; Nakagawa, N. Bull. Chem. Soc. Jpn. 1987, 60, 2463. (g) Peiffer, G.; Courbis, P. Can. J. Chem. 1974, 52, 2894. (h) See also refs 2e, 7c, and 8. For examples with γ,δ-unsaturation within a carbocycle, see: (i) An, Y.-Z.; An, J. G.; Wiemer, D. F. J. Org. Chem. 1994, 59, 8197 and refs cited therein. (j) Castagnino, E.; D'Auria, M.; De Mico, A.; D'Onofrio, F.; Piancatelli, G. J. Chem. Soc., Chem. Commun. 1987, 907. (k) See also ref 12 and refs cited therein.
59. For reactions of alkylphosphonate anions with α,β-unsaturated carboxylic acid chlorides and/or esters, see: (a) Corey, E. J.; Ohuchida, S.; Hahl, R. J. Am. Chem. Soc. 1984, 106, 3875. (b) Mathey, F.; Savignac, P. Tetrahedron 1978, 34, 649. (c) Aboujaoude, E. E.; Collignon, N.; Teulade, M.-P.; Savignac, P. Phosphorus Sulfur 1985, 25, 57. (d) See also refs 2b-d,f. For other methods of preparation, see: (e) Koh, Y. J.; Oh, D. Y. Tetrahedron Lett. 1993, 34, 2147. (f) Tsuge, O.; Kanemasa, S.; Suga, H.; Nakagawa, N. Bull. Chem. Soc. Jpn. 1987, 60, 2463. (g) Peiffer, G.; Courbis, P. Can. J. Chem. 1974, 52, 2894. (h) See also refs 2e, 7c, and 8. For examples with γ,δ-unsaturation within a carbocycle, see: (i) An, Y.-Z.; An, J. G.; Wiemer, D. F. J. Org. Chem. 1994, 59, 8197 and refs cited therein. (j) Castagnino, E.; D'Auria, M.; De Mico, A.; D'Onofrio, F.; Piancatelli, G. J. Chem. Soc., Chem. Commun. 1987, 907. (k) See also ref 12 and refs cited therein.
60. For reactions of alkylphosphonate anions with α,β-unsaturated carboxylic acid chlorides and/or esters, see: (a) Corey, E. J.; Ohuchida, S.; Hahl, R. J. Am. Chem. Soc. 1984, 106, 3875. (b) Mathey, F.; Savignac, P. Tetrahedron 1978, 34, 649. (c) Aboujaoude, E. E.; Collignon, N.; Teulade, M.-P.; Savignac, P. Phosphorus Sulfur 1985, 25, 57. (d) See also refs 2b-d,f. For other methods of preparation, see: (e) Koh, Y. J.; Oh, D. Y. Tetrahedron Lett. 1993, 34, 2147. (f) Tsuge, O.; Kanemasa, S.; Suga, H.; Nakagawa, N. Bull. Chem. Soc. Jpn. 1987, 60, 2463. (g) Peiffer, G.; Courbis, P. Can. J. Chem. 1974, 52, 2894. (h) See also refs 2e, 7c, and 8. For examples with γ,δ-unsaturation within a carbocycle, see: (i) An, Y.-Z.; An, J. G.; Wiemer, D. F. J. Org. Chem. 1994, 59, 8197 and refs cited therein. (j) Castagnino, E.; D'Auria, M.; De Mico, A.; D'Onofrio, F.; Piancatelli, G. J. Chem. Soc., Chem. Commun. 1987, 907. (k) See also ref 12 and refs cited therein.
61. For a review, see: Bhattacharya, A. K.; Thyagarajan, G. Chem. Rev. 1981, 81, 415.
62. Lichtenthaler, F. W. Chem. Rev. 1961, 61, 607.
63. Friesen, R. W.; Phipps, L. G. Synlett 1991, 420.
64. Friesen, R. W.; Kolaczewska, A. E.; Khazanovich, N. Tetrahedron Lett. 1992, 33, 6715.
65. Kolaczewska, A. E. Reactions of Secondary and Tertiary α-Allenic Alcohol Carbamates; M. Sc. Thesis, University of Toronto, 1991.
66. The tertiary α-allenic alcohols 7a-i were prepared from the lithium acetylide of THP protected propargyl alcohol and the appropriate ketones, according to a literature procedure: Cowie, J. S.; Landor, P. D.; Landor, S. R. J. Chem. Soc., Perkin Trans. 1 1973, 720.
67. 3) after 1 h; column chromatography.
68. For experimental details and interpretation of a similar experiment, see ref 17.
69. 15
70. Takahashi, H.; Fujiwara, K.; Otha, M. Bull. Chem. Soc. Jpn. 1962, 35, 1498.
71. For examples on the dehalogenation of α-haloketones under various conditions, see the following papers and refs cited therein: (a) Kamiya, N.; Tanmatu, H.; Ishii, Y. Chem. Lett. 1992, 293. (b) Perez, D.; Greenspoon, N.; Keinan, E. J. Org. Chem. 1987, 52, 5570.
72. For examples on the dehalogenation of α-haloketones under various conditions, see the following papers and refs cited therein: (a) Kamiya, N.; Tanmatu, H.; Ishii, Y. Chem. Lett. 1992, 293. (b) Perez, D.; Greenspoon, N.; Keinan, E. J. Org. Chem. 1987, 52, 5570.
73. 1H NMR spectrum exhibits only two signals that overlap with the ethoxy groups of the phosphonate moiety of 10.
74. For a rationalization on the stereochemical outcome of the reaction, see ref 17.
75. (a) Isager, P.; Thomsen, I.; Torsell, K. B. G. Acta Chem. Scand. 1990, 44, 806.
76. (b) Andrianome, M.; Häberle, K.; Delmond, B. Tetrahedron 1989, 45, 1079.
77. (c) El-Jazouli, M.; Lage, N.; Masson, S.; Thuillier, A. Bull. Soc Chim. Fr. 1988, 883.
78. (d) Andrianorae, M.; Delmond, B. J. Org. Chem. 1988, 53, 542 and refs cited therein.
79. (e) Adams, D. R.; Bhatnagar, S. P.; Cookson, R. C.; Tuddenham, R. M. J. Chem. Soc., Perkin Trans. 1 1975, 1741.
80. The reaction was performed in the dark as a precaution; according to ref 6f, (E)-α-atlantone is known to partially photoisomerize to its Z-isomer when irradiated with a quartz Hg vapor lamp (44% yield of a 1:1.3 E/Z mixture after 1.5 h). When the reaction illustrated in Scheme 2 was conducted under exposure to ambient light, (±)-α-atlantone was obtained as a column chromatography-separable 7.1 E/Z mixture.