Total synthesis of (+)-7-deoxypancratistatin and (+)-7-deoxy-trans-dihydronarciclasine

Heterocycles

Volumn 43, Issue 7, 1996, Pages 1385-1390

  Chida, Noritaka ^a   Jitsuoka, Makoto ^a   Yamamoto, Yoshiyuki ^a   Ohtsuka, Masami ^a   Ogawa, Seiichiro ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001481868     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-96-7481     Document Type: Article

References (38)

1. S. F. Martin, The Alkaloids, Academic Press, New York, 1987, 30, 251.
2. For isolation and biological activities of pancratistatin, see; (a) G. R. Pettit, V. Gaddamide, and G. M. Cragg, J. Nat. Prod., 1984, 47, 1018; G. R. Pettit, V. Gaddamidi, G. M. Cragg, D. L. Herald, and Y. Sagawa, J. Chem. Soc., Chem. Comm., 1984, 1693. 7-Deoxypancratistatin, see (b) S. Ghosal, S. Singh, Y. Kumar, and R. S. Srivastava, Phytochemistry, 1989, 28, 611. 7-Deoxy-trans- dihydronarciclasine, see (c) G. R. Pettit, G. R. Pettit, III, R. A. Backhaus, M. R. Boyd, and A. W. Meerow, J. Nat. Prod., 1993, 56, 1682. Lycoricidine, see (d) T. Okamoto, Y. Torii, and Y. Isogai, Chem. Pharm. Bull., 1968, 16, 1860.
3. For isolation and biological activities of pancratistatin, see; (a) G. R. Pettit, V. Gaddamide, and G. M. Cragg, J. Nat. Prod., 1984, 47, 1018; G. R. Pettit, V. Gaddamidi, G. M. Cragg, D. L. Herald, and Y. Sagawa, J. Chem. Soc., Chem. Comm., 1984, 1693. 7-Deoxypancratistatin, see (b) S. Ghosal, S. Singh, Y. Kumar, and R. S. Srivastava, Phytochemistry, 1989, 28, 611. 7-Deoxy-trans- dihydronarciclasine, see (c) G. R. Pettit, G. R. Pettit, III, R. A. Backhaus, M. R. Boyd, and A. W. Meerow, J. Nat. Prod., 1993, 56, 1682. Lycoricidine, see (d) T. Okamoto, Y. Torii, and Y. Isogai, Chem. Pharm. Bull., 1968, 16, 1860.
4. For isolation and biological activities of pancratistatin, see; (a) G. R. Pettit, V. Gaddamide, and G. M. Cragg, J. Nat. Prod., 1984, 47, 1018; G. R. Pettit, V. Gaddamidi, G. M. Cragg, D. L. Herald, and Y. Sagawa, J. Chem. Soc., Chem. Comm., 1984, 1693. 7-Deoxypancratistatin, see (b) S. Ghosal, S. Singh, Y. Kumar, and R. S. Srivastava, Phytochemistry, 1989, 28, 611. 7-Deoxy-trans- dihydronarciclasine, see (c) G. R. Pettit, G. R. Pettit, III, R. A. Backhaus, M. R. Boyd, and A. W. Meerow, J. Nat. Prod., 1993, 56, 1682. Lycoricidine, see (d) T. Okamoto, Y. Torii, and Y. Isogai, Chem. Pharm. Bull., 1968, 16, 1860.
5. For isolation and biological activities of pancratistatin, see; (a) G. R. Pettit, V. Gaddamide, and G. M. Cragg, J. Nat. Prod., 1984, 47, 1018; G. R. Pettit, V. Gaddamidi, G. M. Cragg, D. L. Herald, and Y. Sagawa, J. Chem. Soc., Chem. Comm., 1984, 1693. 7-Deoxypancratistatin, see (b) S. Ghosal, S. Singh, Y. Kumar, and R. S. Srivastava, Phytochemistry, 1989, 28, 611. 7-Deoxy-trans- dihydronarciclasine, see (c) G. R. Pettit, G. R. Pettit, III, R. A. Backhaus, M. R. Boyd, and A. W. Meerow, J. Nat. Prod., 1993, 56, 1682. Lycoricidine, see (d) T. Okamoto, Y. Torii, and Y. Isogai, Chem. Pharm. Bull., 1968, 16, 1860.
6. For isolation and biological activities of pancratistatin, see; (a) G. R. Pettit, V. Gaddamide, and G. M. Cragg, J. Nat. Prod., 1984, 47, 1018; G. R. Pettit, V. Gaddamidi, G. M. Cragg, D. L. Herald, and Y. Sagawa, J. Chem. Soc., Chem. Comm., 1984, 1693. 7-Deoxypancratistatin, see (b) S. Ghosal, S. Singh, Y. Kumar, and R. S. Srivastava, Phytochemistry, 1989, 28, 611. 7-Deoxy-trans- dihydronarciclasine, see (c) G. R. Pettit, G. R. Pettit, III, R. A. Backhaus, M. R. Boyd, and A. W. Meerow, J. Nat. Prod., 1993, 56, 1682. Lycoricidine, see (d) T. Okamoto, Y. Torii, and Y. Isogai, Chem. Pharm. Bull., 1968, 16, 1860.
7. B. Gabrielsen, T. P. Monath, J. W. Huggins, D. F. Kefauver, G. R. Pettit, G. Groszek, M. Hollingshead, J. J. Kirshi, W. M. Shannon, E. M. Schubert, J. DaRe, B. Ugarkar, M. A. Ussery, and M. J. Phelan, J. Nat. Prod., 1992, 55, 1569.
8. For synthetic approaches to phenanthridone alkaloids, see K. Krohn and A. Mondon, Chem. Ber., 1976, 109, 855; R. S. C. Ropes and C. H. Heathcock, Tetrahedron Lett., 1992, 33, 6775; M. C. McIntosh and S. M. Weinreb, J. Org. Chem., 1993, 58, 4823; T. K. Park and S. J. Danishefsky, Tetrahedron Lett., 1995, 36, 195; T. J. Doyle, M. Hendrix, and J. Haseltine, Tetrahedron Lett., 1994, 35, 8295;
9. For synthetic approaches to phenanthridone alkaloids, see K. Krohn and A. Mondon, Chem. Ber., 1976, 109, 855; R. S. C. Ropes and C. H. Heathcock, Tetrahedron Lett., 1992, 33, 6775; M. C. McIntosh and S. M. Weinreb, J. Org. Chem., 1993, 58, 4823; T. K. Park and S. J. Danishefsky, Tetrahedron Lett., 1995, 36, 195; T. J. Doyle, M. Hendrix, and J. Haseltine, Tetrahedron Lett., 1994, 35, 8295;
10. For synthetic approaches to phenanthridone alkaloids, see K. Krohn and A. Mondon, Chem. Ber., 1976, 109, 855; R. S. C. Ropes and C. H. Heathcock, Tetrahedron Lett., 1992, 33, 6775; M. C. McIntosh and S. M. Weinreb, J. Org. Chem., 1993, 58, 4823; T. K. Park and S. J. Danishefsky, Tetrahedron Lett., 1995, 36, 195; T. J. Doyle, M. Hendrix, and J. Haseltine, Tetrahedron Lett., 1994, 35, 8295;
11. For synthetic approaches to phenanthridone alkaloids, see K. Krohn and A. Mondon, Chem. Ber., 1976, 109, 855; R. S. C. Ropes and C. H. Heathcock, Tetrahedron Lett., 1992, 33, 6775; M. C. McIntosh and S. M. Weinreb, J. Org. Chem., 1993, 58, 4823; T. K. Park and S. J. Danishefsky, Tetrahedron Lett., 1995, 36, 195; T. J. Doyle, M. Hendrix, and J. Haseltine, Tetrahedron Lett., 1994, 35, 8295;
12. For synthetic approaches to phenanthridone alkaloids, see K. Krohn and A. Mondon, Chem. Ber., 1976, 109, 855; R. S. C. Ropes and C. H. Heathcock, Tetrahedron Lett., 1992, 33, 6775; M. C. McIntosh and S. M. Weinreb, J. Org. Chem., 1993, 58, 4823; T. K. Park and S. J. Danishefsky, Tetrahedron Lett., 1995, 36, 195; T. J. Doyle, M. Hendrix, and J. Haseltine, Tetrahedron Lett., 1994, 35, 8295;
13. M. Khaldi, F. Chrétien, and Y. Chapleur, Tetrahedron Lett., 1995, 36, 3003;
14. J. H. Rigby and V. Gupta, Synlett, 1995, 547;
15. R. C. Thompson and J. Kallmerten, J. Org. Chem., 1990, 55, 6076;
16. F. Chrétien, S. I. Ahmed, A. Masion, and Y. Chapleur, Tetrahedron, 1993, 49, 7463.
17. For total Synthesis of racemic pancratistatin, see (a) S. Danishefsky and J. Y. Lee, J. Am. Chem. Soc., 1989, 111, 4829; optically active, see (b) X. Tian, T. Hudlicky, and K. Königsberger, J. Am. Chem. Soc., 1995, 117, 3643; B. M. Trost and S. R. Pulley, J. Am. Chem. Soc., 1995, 117, 10143. Total synthesis of racemic 7-deoxypancratistatin, see (c) S. Ohta and S. Kimoto, Chem. Pharm. Bull., 1976, 24, 2977; optically active, see (d) H. Paulsen and M. Stubbe, Liebigs Ann. Chem., 1983, 535; H. Paulsen and M. Stubbe, Tetrahedron Lett., 1982, 23, 3171; (e) G. E. Keck, S. F. McHardy, and J. A. Murry, J. Am. Chem. Soc., 1995, 117, 7289; (f) X. Tian, R. Maurya, K. Königsberger, and T. Hudlicky, Synlett, 1995, 1125. Total synthesis of racemic lycoricidine, see ref 5c; optically active, see ref 5d; (g) N. Chida, M. Ohtsuka, and S. Ogawa, J. Org. Chem., 1993, 58, 4441; N. Chida, M. Ohtsuka, and S. Ogawa, Tetrahedron Lett., 1991, 32, 4525; (h) T. Hudlicky and H. F. Olivo, J. Am. Chem. Soc., 1992, 114, 9694; T. Hudlicky, H. F. Olivo, and B. J. McKibben, J. Am. Chem. Soc., 1994, 116, 5108; (j) S. F. Martin and H. Tso, Heterocycles, 1993, 35, 85. Total synthesis of racemic 7-deoxy-trans-dihydronarciclasine, see K. Isobe, J. Taga, and Y. Tsuda, Heterocycles, 1978, 9, 625. Conversion of natural lycoricidine into 7-deoxy-trans- dihydronarciclasine, see ref. 3.
18. For total Synthesis of racemic pancratistatin, see (a) S. Danishefsky and J. Y. Lee, J. Am. Chem. Soc., 1989, 111, 4829; optically active, see (b) X. Tian, T. Hudlicky, and K. Königsberger, J. Am. Chem. Soc., 1995, 117, 3643; B. M. Trost and S. R. Pulley, J. Am. Chem. Soc., 1995, 117, 10143. Total synthesis of racemic 7-deoxypancratistatin, see (c) S. Ohta and S. Kimoto, Chem. Pharm. Bull., 1976, 24, 2977; optically active, see (d) H. Paulsen and M. Stubbe, Liebigs Ann. Chem., 1983, 535; H. Paulsen and M. Stubbe, Tetrahedron Lett., 1982, 23, 3171; (e) G. E. Keck, S. F. McHardy, and J. A. Murry, J. Am. Chem. Soc., 1995, 117, 7289; (f) X. Tian, R. Maurya, K. Königsberger, and T. Hudlicky, Synlett, 1995, 1125. Total synthesis of racemic lycoricidine, see ref 5c; optically active, see ref 5d; (g) N. Chida, M. Ohtsuka, and S. Ogawa, J. Org. Chem., 1993, 58, 4441; N. Chida, M. Ohtsuka, and S. Ogawa, Tetrahedron Lett., 1991, 32, 4525; (h) T. Hudlicky and H. F. Olivo, J. Am. Chem. Soc., 1992, 114, 9694; T. Hudlicky, H. F. Olivo, and B. J. McKibben, J. Am. Chem. Soc., 1994, 116, 5108; (j) S. F. Martin and H. Tso, Heterocycles, 1993, 35, 85. Total synthesis of racemic 7-deoxy-trans-dihydronarciclasine, see K. Isobe, J. Taga, and Y. Tsuda, Heterocycles, 1978, 9, 625. Conversion of natural lycoricidine into 7-deoxy-trans- dihydronarciclasine, see ref. 3.
19. For total Synthesis of racemic pancratistatin, see (a) S. Danishefsky and J. Y. Lee, J. Am. Chem. Soc., 1989, 111, 4829; optically active, see (b) X. Tian, T. Hudlicky, and K. Königsberger, J. Am. Chem. Soc., 1995, 117, 3643; B. M. Trost and S. R. Pulley, J. Am. Chem. Soc., 1995, 117, 10143. Total synthesis of racemic 7-deoxypancratistatin, see (c) S. Ohta and S. Kimoto, Chem. Pharm. Bull., 1976, 24, 2977; optically active, see (d) H. Paulsen and M. Stubbe, Liebigs Ann. Chem., 1983, 535; H. Paulsen and M. Stubbe, Tetrahedron Lett., 1982, 23, 3171; (e) G. E. Keck, S. F. McHardy, and J. A. Murry, J. Am. Chem. Soc., 1995, 117, 7289; (f) X. Tian, R. Maurya, K. Königsberger, and T. Hudlicky, Synlett, 1995, 1125. Total synthesis of racemic lycoricidine, see ref 5c; optically active, see ref 5d; (g) N. Chida, M. Ohtsuka, and S. Ogawa, J. Org. Chem., 1993, 58, 4441; N. Chida, M. Ohtsuka, and S. Ogawa, Tetrahedron Lett., 1991, 32, 4525; (h) T. Hudlicky and H. F. Olivo, J. Am. Chem. Soc., 1992, 114, 9694; T. Hudlicky, H. F. Olivo, and B. J. McKibben, J. Am. Chem. Soc., 1994, 116, 5108; (j) S. F. Martin and H. Tso, Heterocycles, 1993, 35, 85. Total synthesis of racemic 7-deoxy-trans-dihydronarciclasine, see K. Isobe, J. Taga, and Y. Tsuda, Heterocycles, 1978, 9, 625. Conversion of natural lycoricidine into 7-deoxy-trans- dihydronarciclasine, see ref. 3.
20. For total Synthesis of racemic pancratistatin, see (a) S. Danishefsky and J. Y. Lee, J. Am. Chem. Soc., 1989, 111, 4829; optically active, see (b) X. Tian, T. Hudlicky, and K. Königsberger, J. Am. Chem. Soc., 1995, 117, 3643; B. M. Trost and S. R. Pulley, J. Am. Chem. Soc., 1995, 117, 10143. Total synthesis of racemic 7-deoxypancratistatin, see (c) S. Ohta and S. Kimoto, Chem. Pharm. Bull., 1976, 24, 2977; optically active, see (d) H. Paulsen and M. Stubbe, Liebigs Ann. Chem., 1983, 535; H. Paulsen and M. Stubbe, Tetrahedron Lett., 1982, 23, 3171; (e) G. E. Keck, S. F. McHardy, and J. A. Murry, J. Am. Chem. Soc., 1995, 117, 7289; (f) X. Tian, R. Maurya, K. Königsberger, and T. Hudlicky, Synlett, 1995, 1125. Total synthesis of racemic lycoricidine, see ref 5c; optically active, see ref 5d; (g) N. Chida, M. Ohtsuka, and S. Ogawa, J. Org. Chem., 1993, 58, 4441; N. Chida, M. Ohtsuka, and S. Ogawa, Tetrahedron Lett., 1991, 32, 4525; (h) T. Hudlicky and H. F. Olivo, J. Am. Chem. Soc., 1992, 114, 9694; T. Hudlicky, H. F. Olivo, and B. J. McKibben, J. Am. Chem. Soc., 1994, 116, 5108; (j) S. F. Martin and H. Tso, Heterocycles, 1993, 35, 85. Total synthesis of racemic 7-deoxy-trans-dihydronarciclasine, see K. Isobe, J. Taga, and Y. Tsuda, Heterocycles, 1978, 9, 625. Conversion of natural lycoricidine into 7-deoxy-trans- dihydronarciclasine, see ref. 3.
21. For total Synthesis of racemic pancratistatin, see (a) S. Danishefsky and J. Y. Lee, J. Am. Chem. Soc., 1989, 111, 4829; optically active, see (b) X. Tian, T. Hudlicky, and K. Königsberger, J. Am. Chem. Soc., 1995, 117, 3643; B. M. Trost and S. R. Pulley, J. Am. Chem. Soc., 1995, 117, 10143. Total synthesis of racemic 7-deoxypancratistatin, see (c) S. Ohta and S. Kimoto, Chem. Pharm. Bull., 1976, 24, 2977; optically active, see (d) H. Paulsen and M. Stubbe, Liebigs Ann. Chem., 1983, 535; H. Paulsen and M. Stubbe, Tetrahedron Lett., 1982, 23, 3171; (e) G. E. Keck, S. F. McHardy, and J. A. Murry, J. Am. Chem. Soc., 1995, 117, 7289; (f) X. Tian, R. Maurya, K. Königsberger, and T. Hudlicky, Synlett, 1995, 1125. Total synthesis of racemic lycoricidine, see ref 5c; optically active, see ref 5d; (g) N. Chida, M. Ohtsuka, and S. Ogawa, J. Org. Chem., 1993, 58, 4441; N. Chida, M. Ohtsuka, and S. Ogawa, Tetrahedron Lett., 1991, 32, 4525; (h) T. Hudlicky and H. F. Olivo, J. Am. Chem. Soc., 1992, 114, 9694; T. Hudlicky, H. F. Olivo, and B. J. McKibben, J. Am. Chem. Soc., 1994, 116, 5108; (j) S. F. Martin and H. Tso, Heterocycles, 1993, 35, 85. Total synthesis of racemic 7-deoxy-trans-dihydronarciclasine, see K. Isobe, J. Taga, and Y. Tsuda, Heterocycles, 1978, 9, 625. Conversion of natural lycoricidine into 7-deoxy-trans- dihydronarciclasine, see ref. 3.
22. For total Synthesis of racemic pancratistatin, see (a) S. Danishefsky and J. Y. Lee, J. Am. Chem. Soc., 1989, 111, 4829; optically active, see (b) X. Tian, T. Hudlicky, and K. Königsberger, J. Am. Chem. Soc., 1995, 117, 3643; B. M. Trost and S. R. Pulley, J. Am. Chem. Soc., 1995, 117, 10143. Total synthesis of racemic 7-deoxypancratistatin, see (c) S. Ohta and S. Kimoto, Chem. Pharm. Bull., 1976, 24, 2977; optically active, see (d) H. Paulsen and M. Stubbe, Liebigs Ann. Chem., 1983, 535; H. Paulsen and M. Stubbe, Tetrahedron Lett., 1982, 23, 3171; (e) G. E. Keck, S. F. McHardy, and J. A. Murry, J. Am. Chem. Soc., 1995, 117, 7289; (f) X. Tian, R. Maurya, K. Königsberger, and T. Hudlicky, Synlett, 1995, 1125. Total synthesis of racemic lycoricidine, see ref 5c; optically active, see ref 5d; (g) N. Chida, M. Ohtsuka, and S. Ogawa, J. Org. Chem., 1993, 58, 4441; N. Chida, M. Ohtsuka, and S. Ogawa, Tetrahedron Lett., 1991, 32, 4525; (h) T. Hudlicky and H. F. Olivo, J. Am. Chem. Soc., 1992, 114, 9694; T. Hudlicky, H. F. Olivo, and B. J. McKibben, J. Am. Chem. Soc., 1994, 116, 5108; (j) S. F. Martin and H. Tso, Heterocycles, 1993, 35, 85. Total synthesis of racemic 7-deoxy-trans-dihydronarciclasine, see K. Isobe, J. Taga, and Y. Tsuda, Heterocycles, 1978, 9, 625. Conversion of natural lycoricidine into 7-deoxy-trans- dihydronarciclasine, see ref. 3.
23. For total Synthesis of racemic pancratistatin, see (a) S. Danishefsky and J. Y. Lee, J. Am. Chem. Soc., 1989, 111, 4829; optically active, see (b) X. Tian, T. Hudlicky, and K. Königsberger, J. Am. Chem. Soc., 1995, 117, 3643; B. M. Trost and S. R. Pulley, J. Am. Chem. Soc., 1995, 117, 10143. Total synthesis of racemic 7-deoxypancratistatin, see (c) S. Ohta and S. Kimoto, Chem. Pharm. Bull., 1976, 24, 2977; optically active, see (d) H. Paulsen and M. Stubbe, Liebigs Ann. Chem., 1983, 535; H. Paulsen and M. Stubbe, Tetrahedron Lett., 1982, 23, 3171; (e) G. E. Keck, S. F. McHardy, and J. A. Murry, J. Am. Chem. Soc., 1995, 117, 7289; (f) X. Tian, R. Maurya, K. Königsberger, and T. Hudlicky, Synlett, 1995, 1125. Total synthesis of racemic lycoricidine, see ref 5c; optically active, see ref 5d; (g) N. Chida, M. Ohtsuka, and S. Ogawa, J. Org. Chem., 1993, 58, 4441; N. Chida, M. Ohtsuka, and S. Ogawa, Tetrahedron Lett., 1991, 32, 4525; (h) T. Hudlicky and H. F. Olivo, J. Am. Chem. Soc., 1992, 114, 9694; T. Hudlicky, H. F. Olivo, and B. J. McKibben, J. Am. Chem. Soc., 1994, 116, 5108; (j) S. F. Martin and H. Tso, Heterocycles, 1993, 35, 85. Total synthesis of racemic 7-deoxy-trans-dihydronarciclasine, see K. Isobe, J. Taga, and Y. Tsuda, Heterocycles, 1978, 9, 625. Conversion of natural lycoricidine into 7-deoxy-trans- dihydronarciclasine, see ref. 3.
24. For total Synthesis of racemic pancratistatin, see (a) S. Danishefsky and J. Y. Lee, J. Am. Chem. Soc., 1989, 111, 4829; optically active, see (b) X. Tian, T. Hudlicky, and K. Königsberger, J. Am. Chem. Soc., 1995, 117, 3643; B. M. Trost and S. R. Pulley, J. Am. Chem. Soc., 1995, 117, 10143. Total synthesis of racemic 7-deoxypancratistatin, see (c) S. Ohta and S. Kimoto, Chem. Pharm. Bull., 1976, 24, 2977; optically active, see (d) H. Paulsen and M. Stubbe, Liebigs Ann. Chem., 1983, 535; H. Paulsen and M. Stubbe, Tetrahedron Lett., 1982, 23, 3171; (e) G. E. Keck, S. F. McHardy, and J. A. Murry, J. Am. Chem. Soc., 1995, 117, 7289; (f) X. Tian, R. Maurya, K. Königsberger, and T. Hudlicky, Synlett, 1995, 1125. Total synthesis of racemic lycoricidine, see ref 5c; optically active, see ref 5d; (g) N. Chida, M. Ohtsuka, and S. Ogawa, J. Org. Chem., 1993, 58, 4441; N. Chida, M. Ohtsuka, and S. Ogawa, Tetrahedron Lett., 1991, 32, 4525; (h) T. Hudlicky and H. F. Olivo, J. Am. Chem. Soc., 1992, 114, 9694; T. Hudlicky, H. F. Olivo, and B. J. McKibben, J. Am. Chem. Soc., 1994, 116, 5108; (j) S. F. Martin and H. Tso, Heterocycles, 1993, 35, 85. Total synthesis of racemic 7-deoxy-trans-dihydronarciclasine, see K. Isobe, J. Taga, and Y. Tsuda, Heterocycles, 1978, 9, 625. Conversion of natural lycoricidine into 7-deoxy-trans- dihydronarciclasine, see ref. 3.
25. For total Synthesis of racemic pancratistatin, see (a) S. Danishefsky and J. Y. Lee, J. Am. Chem. Soc., 1989, 111, 4829; optically active, see (b) X. Tian, T. Hudlicky, and K. Königsberger, J. Am. Chem. Soc., 1995, 117, 3643; B. M. Trost and S. R. Pulley, J. Am. Chem. Soc., 1995, 117, 10143. Total synthesis of racemic 7-deoxypancratistatin, see (c) S. Ohta and S. Kimoto, Chem. Pharm. Bull., 1976, 24, 2977; optically active, see (d) H. Paulsen and M. Stubbe, Liebigs Ann. Chem., 1983, 535; H. Paulsen and M. Stubbe, Tetrahedron Lett., 1982, 23, 3171; (e) G. E. Keck, S. F. McHardy, and J. A. Murry, J. Am. Chem. Soc., 1995, 117, 7289; (f) X. Tian, R. Maurya, K. Königsberger, and T. Hudlicky, Synlett, 1995, 1125. Total synthesis of racemic lycoricidine, see ref 5c; optically active, see ref 5d; (g) N. Chida, M. Ohtsuka, and S. Ogawa, J. Org. Chem., 1993, 58, 4441; N. Chida, M. Ohtsuka, and S. Ogawa, Tetrahedron Lett., 1991, 32, 4525; (h) T. Hudlicky and H. F. Olivo, J. Am. Chem. Soc., 1992, 114, 9694; T. Hudlicky, H. F. Olivo, and B. J. McKibben, J. Am. Chem. Soc., 1994, 116, 5108; (j) S. F. Martin and H. Tso, Heterocycles, 1993, 35, 85. Total synthesis of racemic 7-deoxy-trans-dihydronarciclasine, see K. Isobe, J. Taga, and Y. Tsuda, Heterocycles, 1978, 9, 625. Conversion of natural lycoricidine into 7-deoxy-trans- dihydronarciclasine, see ref. 3.
26. For total Synthesis of racemic pancratistatin, see (a) S. Danishefsky and J. Y. Lee, J. Am. Chem. Soc., 1989, 111, 4829; optically active, see (b) X. Tian, T. Hudlicky, and K. Königsberger, J. Am. Chem. Soc., 1995, 117, 3643; B. M. Trost and S. R. Pulley, J. Am. Chem. Soc., 1995, 117, 10143. Total synthesis of racemic 7-deoxypancratistatin, see (c) S. Ohta and S. Kimoto, Chem. Pharm. Bull., 1976, 24, 2977; optically active, see (d) H. Paulsen and M. Stubbe, Liebigs Ann. Chem., 1983, 535; H. Paulsen and M. Stubbe, Tetrahedron Lett., 1982, 23, 3171; (e) G. E. Keck, S. F. McHardy, and J. A. Murry, J. Am. Chem. Soc., 1995, 117, 7289; (f) X. Tian, R. Maurya, K. Königsberger, and T. Hudlicky, Synlett, 1995, 1125. Total synthesis of racemic lycoricidine, see ref 5c; optically active, see ref 5d; (g) N. Chida, M. Ohtsuka, and S. Ogawa, J. Org. Chem., 1993, 58, 4441; N. Chida, M. Ohtsuka, and S. Ogawa, Tetrahedron Lett., 1991, 32, 4525; (h) T. Hudlicky and H. F. Olivo, J. Am. Chem. Soc., 1992, 114, 9694; T. Hudlicky, H. F. Olivo, and B. J. McKibben, J. Am. Chem. Soc., 1994, 116, 5108; (j) S. F. Martin and H. Tso, Heterocycles, 1993, 35, 85. Total synthesis of racemic 7-deoxy-trans-dihydronarciclasine, see K. Isobe, J. Taga, and Y. Tsuda, Heterocycles, 1978, 9, 625. Conversion of natural lycoricidine into 7-deoxy-trans- dihydronarciclasine, see ref. 3.
27. For total Synthesis of racemic pancratistatin, see (a) S. Danishefsky and J. Y. Lee, J. Am. Chem. Soc., 1989, 111, 4829; optically active, see (b) X. Tian, T. Hudlicky, and K. Königsberger, J. Am. Chem. Soc., 1995, 117, 3643; B. M. Trost and S. R. Pulley, J. Am. Chem. Soc., 1995, 117, 10143. Total synthesis of racemic 7-deoxypancratistatin, see (c) S. Ohta and S. Kimoto, Chem. Pharm. Bull., 1976, 24, 2977; optically active, see (d) H. Paulsen and M. Stubbe, Liebigs Ann. Chem., 1983, 535; H. Paulsen and M. Stubbe, Tetrahedron Lett., 1982, 23, 3171; (e) G. E. Keck, S. F. McHardy, and J. A. Murry, J. Am. Chem. Soc., 1995, 117, 7289; (f) X. Tian, R. Maurya, K. Königsberger, and T. Hudlicky, Synlett, 1995, 1125. Total synthesis of racemic lycoricidine, see ref 5c; optically active, see ref 5d; (g) N. Chida, M. Ohtsuka, and S. Ogawa, J. Org. Chem., 1993, 58, 4441; N. Chida, M. Ohtsuka, and S. Ogawa, Tetrahedron Lett., 1991, 32, 4525; (h) T. Hudlicky and H. F. Olivo, J. Am. Chem. Soc., 1992, 114, 9694; T. Hudlicky, H. F. Olivo, and B. J. McKibben, J. Am. Chem. Soc., 1994, 116, 5108; (j) S. F. Martin and H. Tso, Heterocycles, 1993, 35, 85. Total synthesis of racemic 7-deoxy-trans-dihydronarciclasine, see K. Isobe, J. Taga, and Y. Tsuda, Heterocycles, 1978, 9, 625. Conversion of natural lycoricidine into 7-deoxy-trans- dihydronarciclasine, see ref. 3.
28. For total Synthesis of racemic pancratistatin, see (a) S. Danishefsky and J. Y. Lee, J. Am. Chem. Soc., 1989, 111, 4829; optically active, see (b) X. Tian, T. Hudlicky, and K. Königsberger, J. Am. Chem. Soc., 1995, 117, 3643; B. M. Trost and S. R. Pulley, J. Am. Chem. Soc., 1995, 117, 10143. Total synthesis of racemic 7-deoxypancratistatin, see (c) S. Ohta and S. Kimoto, Chem. Pharm. Bull., 1976, 24, 2977; optically active, see (d) H. Paulsen and M. Stubbe, Liebigs Ann. Chem., 1983, 535; H. Paulsen and M. Stubbe, Tetrahedron Lett., 1982, 23, 3171; (e) G. E. Keck, S. F. McHardy, and J. A. Murry, J. Am. Chem. Soc., 1995, 117, 7289; (f) X. Tian, R. Maurya, K. Königsberger, and T. Hudlicky, Synlett, 1995, 1125. Total synthesis of racemic lycoricidine, see ref 5c; optically active, see ref 5d; (g) N. Chida, M. Ohtsuka, and S. Ogawa, J. Org. Chem., 1993, 58, 4441; N. Chida, M. Ohtsuka, and S. Ogawa, Tetrahedron Lett., 1991, 32, 4525; (h) T. Hudlicky and H. F. Olivo, J. Am. Chem. Soc., 1992, 114, 9694; T. Hudlicky, H. F. Olivo, and B. J. McKibben, J. Am. Chem. Soc., 1994, 116, 5108; (j) S. F. Martin and H. Tso, Heterocycles, 1993, 35, 85. Total synthesis of racemic 7-deoxy-trans-dihydronarciclasine, see K. Isobe, J. Taga, and Y. Tsuda, Heterocycles, 1978, 9, 625. Conversion of natural lycoricidine into 7-deoxy-trans- dihydronarciclasine, see ref. 3.
29. For total Synthesis of racemic pancratistatin, see (a) S. Danishefsky and J. Y. Lee, J. Am. Chem. Soc., 1989, 111, 4829; optically active, see (b) X. Tian, T. Hudlicky, and K. Königsberger, J. Am. Chem. Soc., 1995, 117, 3643; B. M. Trost and S. R. Pulley, J. Am. Chem. Soc., 1995, 117, 10143. Total synthesis of racemic 7-deoxypancratistatin, see (c) S. Ohta and S. Kimoto, Chem. Pharm. Bull., 1976, 24, 2977; optically active, see (d) H. Paulsen and M. Stubbe, Liebigs Ann. Chem., 1983, 535; H. Paulsen and M. Stubbe, Tetrahedron Lett., 1982, 23, 3171; (e) G. E. Keck, S. F. McHardy, and J. A. Murry, J. Am. Chem. Soc., 1995, 117, 7289; (f) X. Tian, R. Maurya, K. Königsberger, and T. Hudlicky, Synlett, 1995, 1125. Total synthesis of racemic lycoricidine, see ref 5c; optically active, see ref 5d; (g) N. Chida, M. Ohtsuka, and S. Ogawa, J. Org. Chem., 1993, 58, 4441; N. Chida, M. Ohtsuka, and S. Ogawa, Tetrahedron Lett., 1991, 32, 4525; (h) T. Hudlicky and H. F. Olivo, J. Am. Chem. Soc., 1992, 114, 9694; T. Hudlicky, H. F. Olivo, and B. J. McKibben, J. Am. Chem. Soc., 1994, 116, 5108; (j) S. F. Martin and H. Tso, Heterocycles, 1993, 35, 85. Total synthesis of racemic 7-deoxy-trans-dihydronarciclasine, see K. Isobe, J. Taga, and Y. Tsuda, Heterocycles, 1978, 9, 625. Conversion of natural lycoricidine into 7-deoxy-trans- dihydronarciclasine, see ref. 3.
30. For total Synthesis of racemic pancratistatin, see (a) S. Danishefsky and J. Y. Lee, J. Am. Chem. Soc., 1989, 111, 4829; optically active, see (b) X. Tian, T. Hudlicky, and K. Königsberger, J. Am. Chem. Soc., 1995, 117, 3643; B. M. Trost and S. R. Pulley, J. Am. Chem. Soc., 1995, 117, 10143. Total synthesis of racemic 7-deoxypancratistatin, see (c) S. Ohta and S. Kimoto, Chem. Pharm. Bull., 1976, 24, 2977; optically active, see (d) H. Paulsen and M. Stubbe, Liebigs Ann. Chem., 1983, 535; H. Paulsen and M. Stubbe, Tetrahedron Lett., 1982, 23, 3171; (e) G. E. Keck, S. F. McHardy, and J. A. Murry, J. Am. Chem. Soc., 1995, 117, 7289; (f) X. Tian, R. Maurya, K. Königsberger, and T. Hudlicky, Synlett, 1995, 1125. Total synthesis of racemic lycoricidine, see ref 5c; optically active, see ref 5d; (g) N. Chida, M. Ohtsuka, and S. Ogawa, J. Org. Chem., 1993, 58, 4441; N. Chida, M. Ohtsuka, and S. Ogawa, Tetrahedron Lett., 1991, 32, 4525; (h) T. Hudlicky and H. F. Olivo, J. Am. Chem. Soc., 1992, 114, 9694; T. Hudlicky, H. F. Olivo, and B. J. McKibben, J. Am. Chem. Soc., 1994, 116, 5108; (j) S. F. Martin and H. Tso, Heterocycles, 1993, 35, 85. Total synthesis of racemic 7-deoxy-trans-dihydronarciclasine, see K. Isobe, J. Taga, and Y. Tsuda, Heterocycles, 1978, 9, 625. Conversion of natural lycoricidine into 7-deoxy-trans- dihydronarciclasine, see ref. 3.
31. R. J. Ferrier and S. Middleton, Chem. Rev., 1993, 93, 2779; N. Chida, M. Ohtsuka, K. Ogura, and S. Ogawa, Bull. Chem. Soc. Jpn., 1991, 64, 2118; N. Chida, K. Sugihara, and S. Ogawa, J. Chem. Soc., Chem. Comm., 1994, 901, and references therein.
32. R. J. Ferrier and S. Middleton, Chem. Rev., 1993, 93, 2779; N. Chida, M. Ohtsuka, K. Ogura, and S. Ogawa, Bull. Chem. Soc. Jpn., 1991, 64, 2118; N. Chida, K. Sugihara, and S. Ogawa, J. Chem. Soc., Chem. Comm., 1994, 901, and references therein.
33. R. J. Ferrier and S. Middleton, Chem. Rev., 1993, 93, 2779; N. Chida, M. Ohtsuka, K. Ogura, and S. Ogawa, Bull. Chem. Soc. Jpn., 1991, 64, 2118; N. Chida, K. Sugihara, and S. Ogawa, J. Chem. Soc., Chem. Comm., 1994, 901, and references therein.
34. 1H nmr, ir and mass spectrometric and/or elemental analyses.
35. 2,3 isomer of compound 12.
36. M. Imuta and H. Ziffer, J. Org. Chem., 1979, 44, 1351.
37. The configuration of the epoxide ring in 15 is not determined but has been tentatively assigned to be β as depicted in Scheme 2, on consideration of the directive effect of the C-3 hydroxy group.
38. When O-acetylation was carried out with acetic anhydride-pyridine, significant amount of eliminated product (N-MPM lycoricidine triacetate) was formed.