Total syntheses of (-)-lycoricidine, (+)-lycoricidine, and (+)- narciclasine via 6-exo cyclizations of substituted vinyl radicals with oxime ethers

Journal of the American Chemical Society

Volumn 121, Issue 22, 1999, Pages 5176-5190

  Keck, Gary E ^a   Wager, Travis T ^a   Duarte Rodriquez, J Felix ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ALKYNE; LYCORICIDINE; NARCICLASINE; OXIME DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOMER; NONHUMAN; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033538324     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9826688     Document Type: Article

References (81)

1. For a review on the Amaryllidaceae alkaloids, see: (a) Martin, S. F. In The Alkaloids; Brossi, A. R., Ed.; Academic Press: New York, 1987; Vol. 30, pp 251-376. For a review of other synthetic work on the Amaryllidaceae alkaloids, see: (b) Polt, R. L. Amaryllidaceae Alkaloids with Antitumor Activity. Organic Synthesis: Theory and Application; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 3, pp 109-148.
2. For a review on the Amaryllidaceae alkaloids, see: (a) Martin, S. F. In The Alkaloids; Brossi, A. R., Ed.; Academic Press: New York, 1987; Vol. 30, pp 251-376. For a review of other synthetic work on the Amaryllidaceae alkaloids, see: (b) Polt, R. L. Amaryllidaceae Alkaloids with Antitumor Activity. Organic Synthesis: Theory and Application; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 3, pp 109-148.
3. For syntheses of pancratistatin, see: (a) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (b) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden, J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. (c) Trost, B. M.; Pulley, S. R. J. Am. Chem. Soc. 1995, 117, 10143. (d) Doyle, T. J.; Hendrix, M.; VanDerveer, D.; Javanmard, S.; Haseltine, J. Tetrahedron, 1997, 53, 11153. (e) Magnus, P.; Sebhat, I. K. J. Am. Chem. Soc. 1998, 120, 5341.
4. For syntheses of pancratistatin, see: (a) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (b) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden, J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. (c) Trost, B. M.; Pulley, S. R. J. Am. Chem. Soc. 1995, 117, 10143. (d) Doyle, T. J.; Hendrix, M.; VanDerveer, D.; Javanmard, S.; Haseltine, J. Tetrahedron, 1997, 53, 11153. (e) Magnus, P.; Sebhat, I. K. J. Am. Chem. Soc. 1998, 120, 5341.
5. For syntheses of pancratistatin, see: (a) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (b) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden, J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. (c) Trost, B. M.; Pulley, S. R. J. Am. Chem. Soc. 1995, 117, 10143. (d) Doyle, T. J.; Hendrix, M.; VanDerveer, D.; Javanmard, S.; Haseltine, J. Tetrahedron, 1997, 53, 11153. (e) Magnus, P.; Sebhat, I. K. J. Am. Chem. Soc. 1998, 120, 5341.
6. For syntheses of pancratistatin, see: (a) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (b) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden, J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. (c) Trost, B. M.; Pulley, S. R. J. Am. Chem. Soc. 1995, 117, 10143. (d) Doyle, T. J.; Hendrix, M.; VanDerveer, D.; Javanmard, S.; Haseltine, J. Tetrahedron, 1997, 53, 11153. (e) Magnus, P.; Sebhat, I. K. J. Am. Chem. Soc. 1998, 120, 5341.
7. For syntheses of pancratistatin, see: (a) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829. (b) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden, J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. (c) Trost, B. M.; Pulley, S. R. J. Am. Chem. Soc. 1995, 117, 10143. (d) Doyle, T. J.; Hendrix, M.; VanDerveer, D.; Javanmard, S.; Haseltine, J. Tetrahedron, 1997, 53, 11153. (e) Magnus, P.; Sebhat, I. K. J. Am. Chem. Soc. 1998, 120, 5341.
8. For syntheses of 7-deoxypancratistatin, see: (a) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2977. (b) Paulsen, H.; Stubbe, M. Liebigs Ann. Chem. 1983, 535. (c) Tian, X.; Maurya, R.; Königsberger, K.; Hudlicky, T. Synlett 1995, 1125. (d) Chida, N.; Iitsuoka, M.; Yamamoto, Y.; Ohtsuka, M.; Ogawa, S. Heterocycles 1996, 43, 1385. (e) Keck, G. E.; McHardy, S. F.; Murry, J. A. J. Am. Chem. Soc. 1995, 117, 7289. (f) Keck, G. E.; Wager, T. T.; McHardy, S. F. J. Org. Chem. 1998, 63, 9164.
9. For syntheses of 7-deoxypancratistatin, see: (a) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2977. (b) Paulsen, H.; Stubbe, M. Liebigs Ann. Chem. 1983, 535. (c) Tian, X.; Maurya, R.; Königsberger, K.; Hudlicky, T. Synlett 1995, 1125. (d) Chida, N.; Iitsuoka, M.; Yamamoto, Y.; Ohtsuka, M.; Ogawa, S. Heterocycles 1996, 43, 1385. (e) Keck, G. E.; McHardy, S. F.; Murry, J. A. J. Am. Chem. Soc. 1995, 117, 7289. (f) Keck, G. E.; Wager, T. T.; McHardy, S. F. J. Org. Chem. 1998, 63, 9164.
10. For syntheses of 7-deoxypancratistatin, see: (a) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2977. (b) Paulsen, H.; Stubbe, M. Liebigs Ann. Chem. 1983, 535. (c) Tian, X.; Maurya, R.; Königsberger, K.; Hudlicky, T. Synlett 1995, 1125. (d) Chida, N.; Iitsuoka, M.; Yamamoto, Y.; Ohtsuka, M.; Ogawa, S. Heterocycles 1996, 43, 1385. (e) Keck, G. E.; McHardy, S. F.; Murry, J. A. J. Am. Chem. Soc. 1995, 117, 7289. (f) Keck, G. E.; Wager, T. T.; McHardy, S. F. J. Org. Chem. 1998, 63, 9164.
11. For syntheses of 7-deoxypancratistatin, see: (a) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2977. (b) Paulsen, H.; Stubbe, M. Liebigs Ann. Chem. 1983, 535. (c) Tian, X.; Maurya, R.; Königsberger, K.; Hudlicky, T. Synlett 1995, 1125. (d) Chida, N.; Iitsuoka, M.; Yamamoto, Y.; Ohtsuka, M.; Ogawa, S. Heterocycles 1996, 43, 1385. (e) Keck, G. E.; McHardy, S. F.; Murry, J. A. J. Am. Chem. Soc. 1995, 117, 7289. (f) Keck, G. E.; Wager, T. T.; McHardy, S. F. J. Org. Chem. 1998, 63, 9164.
12. For syntheses of 7-deoxypancratistatin, see: (a) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2977. (b) Paulsen, H.; Stubbe, M. Liebigs Ann. Chem. 1983, 535. (c) Tian, X.; Maurya, R.; Königsberger, K.; Hudlicky, T. Synlett 1995, 1125. (d) Chida, N.; Iitsuoka, M.; Yamamoto, Y.; Ohtsuka, M.; Ogawa, S. Heterocycles 1996, 43, 1385. (e) Keck, G. E.; McHardy, S. F.; Murry, J. A. J. Am. Chem. Soc. 1995, 117, 7289. (f) Keck, G. E.; Wager, T. T.; McHardy, S. F. J. Org. Chem. 1998, 63, 9164.
13. For syntheses of 7-deoxypancratistatin, see: (a) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2977. (b) Paulsen, H.; Stubbe, M. Liebigs Ann. Chem. 1983, 535. (c) Tian, X.; Maurya, R.; Königsberger, K.; Hudlicky, T. Synlett 1995, 1125. (d) Chida, N.; Iitsuoka, M.; Yamamoto, Y.; Ohtsuka, M.; Ogawa, S. Heterocycles 1996, 43, 1385. (e) Keck, G. E.; McHardy, S. F.; Murry, J. A. J. Am. Chem. Soc. 1995, 117, 7289. (f) Keck, G. E.; Wager, T. T.; McHardy, S. F. J. Org. Chem. 1998, 63, 9164.
14. For syntheses of lycoricidine, see: (a) Ohta, S.; Kimoto, S. Tetrahedron Lett. 1975, 2270. (b) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2969. (c) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2911. (d) Paulsen, H.; Stubbe, M Tetrahedron Lett. 1982, 23, 3171. (e) Paulsen, H.; Stubbe, M. Liebigs Ann. Chem. 1983, 535. (f) Ogawa, S.; Ohtsuka, M.; Chida, N. Tetrahedron Lett. 1991, 32, 4525. (g) Hudlicky, T.; Olivo, H. R. J. Am. Chem. Soc. 1992, 114, 9694. (h) Martin, S. F.; Tso, H.-H. Heterocycles 1993, 35, 85. (i) Ogawa, S.; Ohtsuka, M.; Chida, N. J. Org. Chem. 1993, 58, 4441. (j) Hudlicky, T.; Olivo, H. F.; McKibben, B. J. Am. Chem. Soc. 1994, 116, 5108. For the isolation of lycoricidine and narciclasine, see: (k) Okamoto, T.; Torii, Y.; Isogai, Y. Chem. Pharm. Bull 1968, 16, 1860.
15. For syntheses of lycoricidine, see: (a) Ohta, S.; Kimoto, S. Tetrahedron Lett. 1975, 2270. (b) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2969. (c) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2911. (d) Paulsen, H.; Stubbe, M Tetrahedron Lett. 1982, 23, 3171. (e) Paulsen, H.; Stubbe, M. Liebigs Ann. Chem. 1983, 535. (f) Ogawa, S.; Ohtsuka, M.; Chida, N. Tetrahedron Lett. 1991, 32, 4525. (g) Hudlicky, T.; Olivo, H. R. J. Am. Chem. Soc. 1992, 114, 9694. (h) Martin, S. F.; Tso, H.-H. Heterocycles 1993, 35, 85. (i) Ogawa, S.; Ohtsuka, M.; Chida, N. J. Org. Chem. 1993, 58, 4441. (j) Hudlicky, T.; Olivo, H. F.; McKibben, B. J. Am. Chem. Soc. 1994, 116, 5108. For the isolation of lycoricidine and narciclasine, see: (k) Okamoto, T.; Torii, Y.; Isogai, Y. Chem. Pharm. Bull 1968, 16, 1860.
16. For syntheses of lycoricidine, see: (a) Ohta, S.; Kimoto, S. Tetrahedron Lett. 1975, 2270. (b) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2969. (c) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2911. (d) Paulsen, H.; Stubbe, M Tetrahedron Lett. 1982, 23, 3171. (e) Paulsen, H.; Stubbe, M. Liebigs Ann. Chem. 1983, 535. (f) Ogawa, S.; Ohtsuka, M.; Chida, N. Tetrahedron Lett. 1991, 32, 4525. (g) Hudlicky, T.; Olivo, H. R. J. Am. Chem. Soc. 1992, 114, 9694. (h) Martin, S. F.; Tso, H.-H. Heterocycles 1993, 35, 85. (i) Ogawa, S.; Ohtsuka, M.; Chida, N. J. Org. Chem. 1993, 58, 4441. (j) Hudlicky, T.; Olivo, H. F.; McKibben, B. J. Am. Chem. Soc. 1994, 116, 5108. For the isolation of lycoricidine and narciclasine, see: (k) Okamoto, T.; Torii, Y.; Isogai, Y. Chem. Pharm. Bull 1968, 16, 1860.
17. For syntheses of lycoricidine, see: (a) Ohta, S.; Kimoto, S. Tetrahedron Lett. 1975, 2270. (b) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2969. (c) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2911. (d) Paulsen, H.; Stubbe, M Tetrahedron Lett. 1982, 23, 3171. (e) Paulsen, H.; Stubbe, M. Liebigs Ann. Chem. 1983, 535. (f) Ogawa, S.; Ohtsuka, M.; Chida, N. Tetrahedron Lett. 1991, 32, 4525. (g) Hudlicky, T.; Olivo, H. R. J. Am. Chem. Soc. 1992, 114, 9694. (h) Martin, S. F.; Tso, H.-H. Heterocycles 1993, 35, 85. (i) Ogawa, S.; Ohtsuka, M.; Chida, N. J. Org. Chem. 1993, 58, 4441. (j) Hudlicky, T.; Olivo, H. F.; McKibben, B. J. Am. Chem. Soc. 1994, 116, 5108. For the isolation of lycoricidine and narciclasine, see: (k) Okamoto, T.; Torii, Y.; Isogai, Y. Chem. Pharm. Bull 1968, 16, 1860.
18. For syntheses of lycoricidine, see: (a) Ohta, S.; Kimoto, S. Tetrahedron Lett. 1975, 2270. (b) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2969. (c) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2911. (d) Paulsen, H.; Stubbe, M Tetrahedron Lett. 1982, 23, 3171. (e) Paulsen, H.; Stubbe, M. Liebigs Ann. Chem. 1983, 535. (f) Ogawa, S.; Ohtsuka, M.; Chida, N. Tetrahedron Lett. 1991, 32, 4525. (g) Hudlicky, T.; Olivo, H. R. J. Am. Chem. Soc. 1992, 114, 9694. (h) Martin, S. F.; Tso, H.-H. Heterocycles 1993, 35, 85. (i) Ogawa, S.; Ohtsuka, M.; Chida, N. J. Org. Chem. 1993, 58, 4441. (j) Hudlicky, T.; Olivo, H. F.; McKibben, B. J. Am. Chem. Soc. 1994, 116, 5108. For the isolation of lycoricidine and narciclasine, see: (k) Okamoto, T.; Torii, Y.; Isogai, Y. Chem. Pharm. Bull 1968, 16, 1860.
19. For syntheses of lycoricidine, see: (a) Ohta, S.; Kimoto, S. Tetrahedron Lett. 1975, 2270. (b) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2969. (c) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2911. (d) Paulsen, H.; Stubbe, M Tetrahedron Lett. 1982, 23, 3171. (e) Paulsen, H.; Stubbe, M. Liebigs Ann. Chem. 1983, 535. (f) Ogawa, S.; Ohtsuka, M.; Chida, N. Tetrahedron Lett. 1991, 32, 4525. (g) Hudlicky, T.; Olivo, H. R. J. Am. Chem. Soc. 1992, 114, 9694. (h) Martin, S. F.; Tso, H.-H. Heterocycles 1993, 35, 85. (i) Ogawa, S.; Ohtsuka, M.; Chida, N. J. Org. Chem. 1993, 58, 4441. (j) Hudlicky, T.; Olivo, H. F.; McKibben, B. J. Am. Chem. Soc. 1994, 116, 5108. For the isolation of lycoricidine and narciclasine, see: (k) Okamoto, T.; Torii, Y.; Isogai, Y. Chem. Pharm. Bull 1968, 16, 1860.
20. For syntheses of lycoricidine, see: (a) Ohta, S.; Kimoto, S. Tetrahedron Lett. 1975, 2270. (b) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2969. (c) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2911. (d) Paulsen, H.; Stubbe, M Tetrahedron Lett. 1982, 23, 3171. (e) Paulsen, H.; Stubbe, M. Liebigs Ann. Chem. 1983, 535. (f) Ogawa, S.; Ohtsuka, M.; Chida, N. Tetrahedron Lett. 1991, 32, 4525. (g) Hudlicky, T.; Olivo, H. R. J. Am. Chem. Soc. 1992, 114, 9694. (h) Martin, S. F.; Tso, H.-H. Heterocycles 1993, 35, 85. (i) Ogawa, S.; Ohtsuka, M.; Chida, N. J. Org. Chem. 1993, 58, 4441. (j) Hudlicky, T.; Olivo, H. F.; McKibben, B. J. Am. Chem. Soc. 1994, 116, 5108. For the isolation of lycoricidine and narciclasine, see: (k) Okamoto, T.; Torii, Y.; Isogai, Y. Chem. Pharm. Bull 1968, 16, 1860.
21. For syntheses of lycoricidine, see: (a) Ohta, S.; Kimoto, S. Tetrahedron Lett. 1975, 2270. (b) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2969. (c) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2911. (d) Paulsen, H.; Stubbe, M Tetrahedron Lett. 1982, 23, 3171. (e) Paulsen, H.; Stubbe, M. Liebigs Ann. Chem. 1983, 535. (f) Ogawa, S.; Ohtsuka, M.; Chida, N. Tetrahedron Lett. 1991, 32, 4525. (g) Hudlicky, T.; Olivo, H. R. J. Am. Chem. Soc. 1992, 114, 9694. (h) Martin, S. F.; Tso, H.-H. Heterocycles 1993, 35, 85. (i) Ogawa, S.; Ohtsuka, M.; Chida, N. J. Org. Chem. 1993, 58, 4441. (j) Hudlicky, T.; Olivo, H. F.; McKibben, B. J. Am. Chem. Soc. 1994, 116, 5108. For the isolation of lycoricidine and narciclasine, see: (k) Okamoto, T.; Torii, Y.; Isogai, Y. Chem. Pharm. Bull 1968, 16, 1860.
22. For syntheses of lycoricidine, see: (a) Ohta, S.; Kimoto, S. Tetrahedron Lett. 1975, 2270. (b) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2969. (c) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2911. (d) Paulsen, H.; Stubbe, M Tetrahedron Lett. 1982, 23, 3171. (e) Paulsen, H.; Stubbe, M. Liebigs Ann. Chem. 1983, 535. (f) Ogawa, S.; Ohtsuka, M.; Chida, N. Tetrahedron Lett. 1991, 32, 4525. (g) Hudlicky, T.; Olivo, H. R. J. Am. Chem. Soc. 1992, 114, 9694. (h) Martin, S. F.; Tso, H.-H. Heterocycles 1993, 35, 85. (i) Ogawa, S.; Ohtsuka, M.; Chida, N. J. Org. Chem. 1993, 58, 4441. (j) Hudlicky, T.; Olivo, H. F.; McKibben, B. J. Am. Chem. Soc. 1994, 116, 5108. For the isolation of lycoricidine and narciclasine, see: (k) Okamoto, T.; Torii, Y.; Isogai, Y. Chem. Pharm. Bull 1968, 16, 1860.
23. For syntheses of lycoricidine, see: (a) Ohta, S.; Kimoto, S. Tetrahedron Lett. 1975, 2270. (b) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2969. (c) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2911. (d) Paulsen, H.; Stubbe, M Tetrahedron Lett. 1982, 23, 3171. (e) Paulsen, H.; Stubbe, M. Liebigs Ann. Chem. 1983, 535. (f) Ogawa, S.; Ohtsuka, M.; Chida, N. Tetrahedron Lett. 1991, 32, 4525. (g) Hudlicky, T.; Olivo, H. R. J. Am. Chem. Soc. 1992, 114, 9694. (h) Martin, S. F.; Tso, H.-H. Heterocycles 1993, 35, 85. (i) Ogawa, S.; Ohtsuka, M.; Chida, N. J. Org. Chem. 1993, 58, 4441. (j) Hudlicky, T.; Olivo, H. F.; McKibben, B. J. Am. Chem. Soc. 1994, 116, 5108. For the isolation of lycoricidine and narciclasine, see: (k) Okamoto, T.; Torii, Y.; Isogai, Y. Chem. Pharm. Bull 1968, 16, 1860.
24. For syntheses of lycoricidine, see: (a) Ohta, S.; Kimoto, S. Tetrahedron Lett. 1975, 2270. (b) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2969. (c) Ohta, S.; Kimoto, S. Chem. Pharm. Bull. 1976, 24, 2911. (d) Paulsen, H.; Stubbe, M Tetrahedron Lett. 1982, 23, 3171. (e) Paulsen, H.; Stubbe, M. Liebigs Ann. Chem. 1983, 535. (f) Ogawa, S.; Ohtsuka, M.; Chida, N. Tetrahedron Lett. 1991, 32, 4525. (g) Hudlicky, T.; Olivo, H. R. J. Am. Chem. Soc. 1992, 114, 9694. (h) Martin, S. F.; Tso, H.-H. Heterocycles 1993, 35, 85. (i) Ogawa, S.; Ohtsuka, M.; Chida, N. J. Org. Chem. 1993, 58, 4441. (j) Hudlicky, T.; Olivo, H. F.; McKibben, B. J. Am. Chem. Soc. 1994, 116, 5108. For the isolation of lycoricidine and narciclasine, see: (k) Okamoto, T.; Torii, Y.; Isogai, Y. Chem. Pharm. Bull 1968, 16, 1860.
25. (a) Rigby, J. H.; Mateo, M. E. J. Am. Chem. Soc. 1997, 119, 12655.
26. (b) For the isolation of narciclasine, see: Piozzi, F.; Modelli, R.; Fuganti, C.; Ceriotti, G. Tetrahedron 1968, 24, 1119.
27. (c) For the isolation of narciclasine 4-O-β-glucoside, see: Abou-Donia, A. H.; De Giulio, A.; Evidente, A.; Gaber, M.; Habib, A.-A.; Lanzetta, R.; Seif El Din, A. A. Phytochemistry 1991, 30, 3445.
28. For additional earlier examples see ref 3e and references therein, (a) Marco-Contelles, J.; Destabel, C.; Chiara, J. L.; Bernabe, M.Tetrahedron Asymmetry 1995, 6, 1547. (b) Naitio, T.; Ninomiya, I.; Tajiri, K.; Kiguchi, T. Tetrahedron Lett. 1995, 36, 253. (c) Marco-Contelles, J.; Chiara, J. L.; Khiar, N.; Gallego, P.; Destabel, C.; Bernabe, M. J. Org. Chem. 1995, 60, 6010. (d) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927. (e) Booth, S. E.; Jenkins, P. R.; Swain, C. J.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. I 1994, 3499. (f) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3933. (g) Grissom, J. W.; Klingberg, D. J. Org. Chem. 1993, 58, 6559. (h) Pattenden, G.; Schulz, D. J. Tetrahedron Lett. 1993, 34, 6787, (i) Enholm, E. J.; Burroff, J. A.; Jaramillo, L. M. Tetrahedron Lett. 1990, 31 3727.
29. For additional earlier examples see ref 3e and references therein, (a) Marco-Contelles, J.; Destabel, C.; Chiara, J. L.; Bernabe, M.Tetrahedron Asymmetry 1995, 6, 1547. (b) Naitio, T.; Ninomiya, I.; Tajiri, K.; Kiguchi, T. Tetrahedron Lett. 1995, 36, 253. (c) Marco-Contelles, J.; Chiara, J. L.; Khiar, N.; Gallego, P.; Destabel, C.; Bernabe, M. J. Org. Chem. 1995, 60, 6010. (d) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927. (e) Booth, S. E.; Jenkins, P. R.; Swain, C. J.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. I 1994, 3499. (f) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3933. (g) Grissom, J. W.; Klingberg, D. J. Org. Chem. 1993, 58, 6559. (h) Pattenden, G.; Schulz, D. J. Tetrahedron Lett. 1993, 34, 6787, (i) Enholm, E. J.; Burroff, J. A.; Jaramillo, L. M. Tetrahedron Lett. 1990, 31 3727.
30. For additional earlier examples see ref 3e and references therein, (a) Marco-Contelles, J.; Destabel, C.; Chiara, J. L.; Bernabe, M.Tetrahedron Asymmetry 1995, 6, 1547. (b) Naitio, T.; Ninomiya, I.; Tajiri, K.; Kiguchi, T. Tetrahedron Lett. 1995, 36, 253. (c) Marco-Contelles, J.; Chiara, J. L.; Khiar, N.; Gallego, P.; Destabel, C.; Bernabe, M. J. Org. Chem. 1995, 60, 6010. (d) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927. (e) Booth, S. E.; Jenkins, P. R.; Swain, C. J.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. I 1994, 3499. (f) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3933. (g) Grissom, J. W.; Klingberg, D. J. Org. Chem. 1993, 58, 6559. (h) Pattenden, G.; Schulz, D. J. Tetrahedron Lett. 1993, 34, 6787, (i) Enholm, E. J.; Burroff, J. A.; Jaramillo, L. M. Tetrahedron Lett. 1990, 31 3727.
31. For additional earlier examples see ref 3e and references therein, (a) Marco-Contelles, J.; Destabel, C.; Chiara, J. L.; Bernabe, M.Tetrahedron Asymmetry 1995, 6, 1547. (b) Naitio, T.; Ninomiya, I.; Tajiri, K.; Kiguchi, T. Tetrahedron Lett. 1995, 36, 253. (c) Marco-Contelles, J.; Chiara, J. L.; Khiar, N.; Gallego, P.; Destabel, C.; Bernabe, M. J. Org. Chem. 1995, 60, 6010. (d) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927. (e) Booth, S. E.; Jenkins, P. R.; Swain, C. J.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. I 1994, 3499. (f) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3933. (g) Grissom, J. W.; Klingberg, D. J. Org. Chem. 1993, 58, 6559. (h) Pattenden, G.; Schulz, D. J. Tetrahedron Lett. 1993, 34, 6787, (i) Enholm, E. J.; Burroff, J. A.; Jaramillo, L. M. Tetrahedron Lett. 1990, 31 3727.
32. For additional earlier examples see ref 3e and references therein, (a) Marco-Contelles, J.; Destabel, C.; Chiara, J. L.; Bernabe, M.Tetrahedron Asymmetry 1995, 6, 1547. (b) Naitio, T.; Ninomiya, I.; Tajiri, K.; Kiguchi, T. Tetrahedron Lett. 1995, 36, 253. (c) Marco-Contelles, J.; Chiara, J. L.; Khiar, N.; Gallego, P.; Destabel, C.; Bernabe, M. J. Org. Chem. 1995, 60, 6010. (d) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927. (e) Booth, S. E.; Jenkins, P. R.; Swain, C. J.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. I 1994, 3499. (f) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3933. (g) Grissom, J. W.; Klingberg, D. J. Org. Chem. 1993, 58, 6559. (h) Pattenden, G.; Schulz, D. J. Tetrahedron Lett. 1993, 34, 6787, (i) Enholm, E. J.; Burroff, J. A.; Jaramillo, L. M. Tetrahedron Lett. 1990, 31 3727.
33. For additional earlier examples see ref 3e and references therein, (a) Marco-Contelles, J.; Destabel, C.; Chiara, J. L.; Bernabe, M.Tetrahedron Asymmetry 1995, 6, 1547. (b) Naitio, T.; Ninomiya, I.; Tajiri, K.; Kiguchi, T. Tetrahedron Lett. 1995, 36, 253. (c) Marco-Contelles, J.; Chiara, J. L.; Khiar, N.; Gallego, P.; Destabel, C.; Bernabe, M. J. Org. Chem. 1995, 60, 6010. (d) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927. (e) Booth, S. E.; Jenkins, P. R.; Swain, C. J.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. I 1994, 3499. (f) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3933. (g) Grissom, J. W.; Klingberg, D. J. Org. Chem. 1993, 58, 6559. (h) Pattenden, G.; Schulz, D. J. Tetrahedron Lett. 1993, 34, 6787, (i) Enholm, E. J.; Burroff, J. A.; Jaramillo, L. M. Tetrahedron Lett. 1990, 31 3727.
34. For additional earlier examples see ref 3e and references therein, (a) Marco-Contelles, J.; Destabel, C.; Chiara, J. L.; Bernabe, M.Tetrahedron Asymmetry 1995, 6, 1547. (b) Naitio, T.; Ninomiya, I.; Tajiri, K.; Kiguchi, T. Tetrahedron Lett. 1995, 36, 253. (c) Marco-Contelles, J.; Chiara, J. L.; Khiar, N.; Gallego, P.; Destabel, C.; Bernabe, M. J. Org. Chem. 1995, 60, 6010. (d) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927. (e) Booth, S. E.; Jenkins, P. R.; Swain, C. J.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. I 1994, 3499. (f) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3933. (g) Grissom, J. W.; Klingberg, D. J. Org. Chem. 1993, 58, 6559. (h) Pattenden, G.; Schulz, D. J. Tetrahedron Lett. 1993, 34, 6787, (i) Enholm, E. J.; Burroff, J. A.; Jaramillo, L. M. Tetrahedron Lett. 1990, 31 3727.
35. For additional earlier examples see ref 3e and references therein, (a) Marco-Contelles, J.; Destabel, C.; Chiara, J. L.; Bernabe, M.Tetrahedron Asymmetry 1995, 6, 1547. (b) Naitio, T.; Ninomiya, I.; Tajiri, K.; Kiguchi, T. Tetrahedron Lett. 1995, 36, 253. (c) Marco-Contelles, J.; Chiara, J. L.; Khiar, N.; Gallego, P.; Destabel, C.; Bernabe, M. J. Org. Chem. 1995, 60, 6010. (d) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927. (e) Booth, S. E.; Jenkins, P. R.; Swain, C. J.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. I 1994, 3499. (f) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3933. (g) Grissom, J. W.; Klingberg, D. J. Org. Chem. 1993, 58, 6559. (h) Pattenden, G.; Schulz, D. J. Tetrahedron Lett. 1993, 34, 6787, (i) Enholm, E. J.; Burroff, J. A.; Jaramillo, L. M. Tetrahedron Lett. 1990, 31 3727.
36. For additional earlier examples see ref 3e and references therein, (a) Marco-Contelles, J.; Destabel, C.; Chiara, J. L.; Bernabe, M.Tetrahedron Asymmetry 1995, 6, 1547. (b) Naitio, T.; Ninomiya, I.; Tajiri, K.; Kiguchi, T. Tetrahedron Lett. 1995, 36, 253. (c) Marco-Contelles, J.; Chiara, J. L.; Khiar, N.; Gallego, P.; Destabel, C.; Bernabe, M. J. Org. Chem. 1995, 60, 6010. (d) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927. (e) Booth, S. E.; Jenkins, P. R.; Swain, C. J.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. I 1994, 3499. (f) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3933. (g) Grissom, J. W.; Klingberg, D. J. Org. Chem. 1993, 58, 6559. (h) Pattenden, G.; Schulz, D. J. Tetrahedron Lett. 1993, 34, 6787, (i) Enholm, E. J.; Burroff, J. A.; Jaramillo, L. M. Tetrahedron Lett. 1990, 31 3727.
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67. (c) Further studies on the scope and generality of this process will be reported separately.
68. 2 reduction step, precluding formation of the B ring. It should also be noted that the vinyl sulfide is not removed in satisfactory yield unless the B-ring is closed.
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77. The minor oxime isomer was characterized in this instance because a similar compound prepared by us (TBS ether version, ent-lycoricidine case) was isolated as the major oxime isomer and was fully characterized.
78. Brown, H. C.; Tsukamoto, A. J. Am. Chem. Soc. 1964, 88, 1089.
79. (a) Yields for this reaction range from 20 to 50%.
80. (b) Yields for this reaction ranged from 14 to 56%.
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