Synthesis of the AB spiroketal subunit of spongistatin 1 (Altohyrtin A): The pyrone approach

Tetrahedron Letters

Volumn 39, Issue 41, 1998, Pages 7487-7490

  Crimmins, Michael T ^a   Washburn, David G ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; COPPER; NATURAL PRODUCT; PYRONE DERIVATIVE; SPONGISTATIN 1; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR OVERHAUSER EFFECT; REACTION ANALYSIS; SPONGE (PORIFERA); STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0032497602     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01629-3     Document Type: Article

References (36)

1. 1. Pettit, G.R.; Cichacz, Z.A.; Gao, F.; Herald, C.L.; Boyd, M.R.; Schmidt, J.M.; Hooper, J.N.A. J. Org. Chem. 1993, 58, 1302-1304. Pettit, G.R.; Cichacz, Z.A.; Herald, C.L.; Gao, F.; Boyd, M.R.; Schmidt, J.M.; Hamel, E. Bai, R. J. Chem. Soc. Chem. Commun. 1994, 1605-1606. Pettit, G.R.; Herald, C.L.; Cichacz, Z.A.; Gao, F.; Schmidt, J.M.; Boyd, M.R.; Christie, N.D.; Boettner, F.E. J. Chem. Soc. Chem. Commun. 1993, 1805-1807. Pettit, G.R.; Herald, C.L.; Cichacz, Z.A.; Gao, F.; Schmidt, J.M.; Boyd, M.R.; Christie, N.D.; Boettner, F.E. J. Chem. Soc. Chem. Commun. 1993, 1166-1168.
2. 1. Pettit, G.R.; Cichacz, Z.A.; Gao, F.; Herald, C.L.; Boyd, M.R.; Schmidt, J.M.; Hooper, J.N.A. J. Org. Chem. 1993, 58, 1302-1304. Pettit, G.R.; Cichacz, Z.A.; Herald, C.L.; Gao, F.; Boyd, M.R.; Schmidt, J.M.; Hamel, E. Bai, R. J. Chem. Soc. Chem. Commun. 1994, 1605-1606. Pettit, G.R.; Herald, C.L.; Cichacz, Z.A.; Gao, F.; Schmidt, J.M.; Boyd, M.R.; Christie, N.D.; Boettner, F.E. J. Chem. Soc. Chem. Commun. 1993, 1805-1807. Pettit, G.R.; Herald, C.L.; Cichacz, Z.A.; Gao, F.; Schmidt, J.M.; Boyd, M.R.; Christie, N.D.; Boettner, F.E. J. Chem. Soc. Chem. Commun. 1993, 1166-1168.
3. 1. Pettit, G.R.; Cichacz, Z.A.; Gao, F.; Herald, C.L.; Boyd, M.R.; Schmidt, J.M.; Hooper, J.N.A. J. Org. Chem. 1993, 58, 1302-1304. Pettit, G.R.; Cichacz, Z.A.; Herald, C.L.; Gao, F.; Boyd, M.R.; Schmidt, J.M.; Hamel, E. Bai, R. J. Chem. Soc. Chem. Commun. 1994, 1605-1606. Pettit, G.R.; Herald, C.L.; Cichacz, Z.A.; Gao, F.; Schmidt, J.M.; Boyd, M.R.; Christie, N.D.; Boettner, F.E. J. Chem. Soc. Chem. Commun. 1993, 1805-1807. Pettit, G.R.; Herald, C.L.; Cichacz, Z.A.; Gao, F.; Schmidt, J.M.; Boyd, M.R.; Christie, N.D.; Boettner, F.E. J. Chem. Soc. Chem. Commun. 1993, 1166-1168.
4. 1. Pettit, G.R.; Cichacz, Z.A.; Gao, F.; Herald, C.L.; Boyd, M.R.; Schmidt, J.M.; Hooper, J.N.A. J. Org. Chem. 1993, 58, 1302-1304. Pettit, G.R.; Cichacz, Z.A.; Herald, C.L.; Gao, F.; Boyd, M.R.; Schmidt, J.M.; Hamel, E. Bai, R. J. Chem. Soc. Chem. Commun. 1994, 1605-1606. Pettit, G.R.; Herald, C.L.; Cichacz, Z.A.; Gao, F.; Schmidt, J.M.; Boyd, M.R.; Christie, N.D.; Boettner, F.E. J. Chem. Soc. Chem. Commun. 1993, 1805-1807. Pettit, G.R.; Herald, C.L.; Cichacz, Z.A.; Gao, F.; Schmidt, J.M.; Boyd, M.R.; Christie, N.D.; Boettner, F.E. J. Chem. Soc. Chem. Commun. 1993, 1166-1168.
5. 2. Kobayashi, M.; Aoki, S.; Sakai, H.; Kawazoe, K.; Kihara, N.; Sasaki, T.; Kitagawa, I. Tetrahedron Lett. 1993, 34, 2795-2798. Kobayashi, M.; Aoki, S.; Kitagawa, I. Tetrahedron Lett. 1994, 35, 1243-1246. Kobayashi, M.; Aoki, S.; Sakai, H.; Kihara, N.; Sasaki, T.; Kitagawa, I. Chem. Pharm. Bull. 1993, 41, 989-991.
6. 2. Kobayashi, M.; Aoki, S.; Sakai, H.; Kawazoe, K.; Kihara, N.; Sasaki, T.; Kitagawa, I. Tetrahedron Lett. 1993, 34, 2795-2798. Kobayashi, M.; Aoki, S.; Kitagawa, I. Tetrahedron Lett. 1994, 35, 1243-1246. Kobayashi, M.; Aoki, S.; Sakai, H.; Kihara, N.; Sasaki, T.; Kitagawa, I. Chem. Pharm. Bull. 1993, 41, 989-991.
7. 2. Kobayashi, M.; Aoki, S.; Sakai, H.; Kawazoe, K.; Kihara, N.; Sasaki, T.; Kitagawa, I. Tetrahedron Lett. 1993, 34, 2795-2798. Kobayashi, M.; Aoki, S.; Kitagawa, I. Tetrahedron Lett. 1994, 35, 1243-1246. Kobayashi, M.; Aoki, S.; Sakai, H.; Kihara, N.; Sasaki, T.; Kitagawa, I. Chem. Pharm. Bull. 1993, 41, 989-991.
8. 3. Fusetani, N.; Shinoda, K.; Matsunaga, S. J. Am. Chem. Soc. 1993, 115, 3977-3981.
9. 4. Bai, R.; Cichacz, Z.A.; Herald, C.L.; Pettit, G.R.; Hamel, E. Mol. Pharmacol. 1993, 44, 757-766. Bai, R.; Taylor, G.F.; Cichacz, Z.A.; Herald, C.L.; Kepler, J.A.; Pettit, G.R.; Hamel, E. Biochemistry 1995, 34, 9714-9721.
10. 4. Bai, R.; Cichacz, Z.A.; Herald, C.L.; Pettit, G.R.; Hamel, E. Mol. Pharmacol. 1993, 44, 757-766. Bai, R.; Taylor, G.F.; Cichacz, Z.A.; Herald, C.L.; Kepler, J.A.; Pettit, G.R.; Hamel, E. Biochemistry 1995, 34, 9714-9721.
11. 5. Claffey, M.M.; Heathcock, C.H. J. Org. Chem. 1996, 61, 7646-7647. Paterson, I.; Oballa, R.M.; Norcross, R.D. Tetrahedron Lett. 1996, 37, 8581-8584. Paquette, L.A.; Zuev, D. Tetrahedron Lett. 1997, 38, 5115-5118. Smith, A.B., III; Lin, Q.; Nakayama, K.; Boldi, A.; Brook, C.S.; McBriar, M.D.; Moser, W.H.; Sobukawa, M.; Zhuang, L. Tetrahedron Lett. 1997, 38, 8675-8678.
12. 5. Claffey, M.M.; Heathcock, C.H. J. Org. Chem. 1996, 61, 7646-7647. Paterson, I.; Oballa, R.M.; Norcross, R.D. Tetrahedron Lett. 1996, 37, 8581-8584. Paquette, L.A.; Zuev, D. Tetrahedron Lett. 1997, 38, 5115-5118. Smith, A.B., III; Lin, Q.; Nakayama, K.; Boldi, A.; Brook, C.S.; McBriar, M.D.; Moser, W.H.; Sobukawa, M.; Zhuang, L. Tetrahedron Lett. 1997, 38, 8675-8678.
13. 5. Claffey, M.M.; Heathcock, C.H. J. Org. Chem. 1996, 61, 7646-7647. Paterson, I.; Oballa, R.M.; Norcross, R.D. Tetrahedron Lett. 1996, 37, 8581-8584. Paquette, L.A.; Zuev, D. Tetrahedron Lett. 1997, 38, 5115-5118. Smith, A.B., III; Lin, Q.; Nakayama, K.; Boldi, A.; Brook, C.S.; McBriar, M.D.; Moser, W.H.; Sobukawa, M.; Zhuang, L. Tetrahedron Lett. 1997, 38, 8675-8678.
14. 5. Claffey, M.M.; Heathcock, C.H. J. Org. Chem. 1996, 61, 7646-7647. Paterson, I.; Oballa, R.M.; Norcross, R.D. Tetrahedron Lett. 1996, 37, 8581-8584. Paquette, L.A.; Zuev, D. Tetrahedron Lett. 1997, 38, 5115-5118. Smith, A.B., III; Lin, Q.; Nakayama, K.; Boldi, A.; Brook, C.S.; McBriar, M.D.; Moser, W.H.; Sobukawa, M.; Zhuang, L. Tetrahedron Lett. 1997, 38, 8675-8678.
15. 6. Hayes, C.J.; Heathcock, C.H. J. Org. Chem. 1997, 62, 2678-2679. Paquette, L.A.; Braun, A. Tetrahedron Lett. 1997, 38, 5119-5122. Smith, A.B., III; Zhuang, L.; Brook, C.S.; Lin, Q.; Moser, W.H.; Trout, R.E.L.; Boldi, A. Tetrahedron Lett. 1997, 38, 8671-8674. Zemribo, R.; Mead, K.T. Tetrahedron Lett. 1998, 39, 3895-3898.
16. 6. Hayes, C.J.; Heathcock, C.H. J. Org. Chem. 1997, 62, 2678-2679. Paquette, L.A.; Braun, A. Tetrahedron Lett. 1997, 38, 5119-5122. Smith, A.B., III; Zhuang, L.; Brook, C.S.; Lin, Q.; Moser, W.H.; Trout, R.E.L.; Boldi, A. Tetrahedron Lett. 1997, 38, 8671-8674. Zemribo, R.; Mead, K.T. Tetrahedron Lett. 1998, 39, 3895-3898.
17. 6. Hayes, C.J.; Heathcock, C.H. J. Org. Chem. 1997, 62, 2678-2679. Paquette, L.A.; Braun, A. Tetrahedron Lett. 1997, 38, 5119-5122. Smith, A.B., III; Zhuang, L.; Brook, C.S.; Lin, Q.; Moser, W.H.; Trout, R.E.L.; Boldi, A. Tetrahedron Lett. 1997, 38, 8671-8674. Zemribo, R.; Mead, K.T. Tetrahedron Lett. 1998, 39, 3895-3898.
18. 6. Hayes, C.J.; Heathcock, C.H. J. Org. Chem. 1997, 62, 2678-2679. Paquette, L.A.; Braun, A. Tetrahedron Lett. 1997, 38, 5119-5122. Smith, A.B., III; Zhuang, L.; Brook, C.S.; Lin, Q.; Moser, W.H.; Trout, R.E.L.; Boldi, A. Tetrahedron Lett. 1997, 38, 8671-8674. Zemribo, R.; Mead, K.T. Tetrahedron Lett. 1998, 39, 3895-3898.
19. 7. Paterson, I.; Keown, L.E. Tetrahedron Lett. 1997, 38, 5727-5730. Lemaire-Audoire, S.; Vogel, P. Tetrahedron Lett. 1998, 39, 1345-1348. Smith, A.B., III; Zhuang, L.; Brook, C.S.; Boldi, A.; McBriar, M.D.; Moser, W.H.; Murase, N.; Nakayama, K.; Verhoest, P.R.; Lin, Q. Tetrahedron Lett. 1997, 38, 8667-8670.
20. 7. Paterson, I.; Keown, L.E. Tetrahedron Lett. 1997, 38, 5727-5730. Lemaire-Audoire, S.; Vogel, P. Tetrahedron Lett. 1998, 39, 1345-1348. Smith, A.B., III; Zhuang, L.; Brook, C.S.; Boldi, A.; McBriar, M.D.; Moser, W.H.; Murase, N.; Nakayama, K.; Verhoest, P.R.; Lin, Q. Tetrahedron Lett. 1997, 38, 8667-8670.
21. 7. Paterson, I.; Keown, L.E. Tetrahedron Lett. 1997, 38, 5727-5730. Lemaire-Audoire, S.; Vogel, P. Tetrahedron Lett. 1998, 39, 1345-1348. Smith, A.B., III; Zhuang, L.; Brook, C.S.; Boldi, A.; McBriar, M.D.; Moser, W.H.; Murase, N.; Nakayama, K.; Verhoest, P.R.; Lin, Q. Tetrahedron Lett. 1997, 38, 8667-8670.
22. 8. Evans, D.A.; Coleman, P.J.; Diaz, L.C. Angew. Chem. Int. Ed. Engl. 1997, 36, 2738-2741. Evans, D.A.; Trotter, B.W.; Cote, B.; Coleman, P.J. Angew. Chem. Int. Ed. Engl. 1997, 36, 2741-2744. Evans, D.A.; Trotter, B.W.; Cote, B.; Coleman, P.J.; Diaz, L.C.; Tyler, A.N. Angew. Chem. Int. Ed. Engl. 1997, 36, 2744-2747.
23. 8. Evans, D.A.; Coleman, P.J.; Diaz, L.C. Angew. Chem. Int. Ed. Engl. 1997, 36, 2738-2741. Evans, D.A.; Trotter, B.W.; Cote, B.; Coleman, P.J. Angew. Chem. Int. Ed. Engl. 1997, 36, 2741-2744. Evans, D.A.; Trotter, B.W.; Cote, B.; Coleman, P.J.; Diaz, L.C.; Tyler, A.N. Angew. Chem. Int. Ed. Engl. 1997, 36, 2744-2747.
24. 8. Evans, D.A.; Coleman, P.J.; Diaz, L.C. Angew. Chem. Int. Ed. Engl. 1997, 36, 2738-2741. Evans, D.A.; Trotter, B.W.; Cote, B.; Coleman, P.J. Angew. Chem. Int. Ed. Engl. 1997, 36, 2741-2744. Evans, D.A.; Trotter, B.W.; Cote, B.; Coleman, P.J.; Diaz, L.C.; Tyler, A.N. Angew. Chem. Int. Ed. Engl. 1997, 36, 2744-2747.
25. 9. Guo, J.; Duffy, K.J.; Stevens, K.L.; Dalko, P.I.; Roth, R.M.; Hayward, M.M.; Kishi, Y. Angew. Chem. Int. Ed. Engl. 1998, 37, 187-192. Hayward, M.M.; Roth, R.M.; Duffy, K.J.; Dalko, P.I.; Stevens, K.L.; Guo, J.; Kishi, Y. Angew. Chem. Int. Ed. Engl. 1998, 37, 192-196.
26. 9. Guo, J.; Duffy, K.J.; Stevens, K.L.; Dalko, P.I.; Roth, R.M.; Hayward, M.M.; Kishi, Y. Angew. Chem. Int. Ed. Engl. 1998, 37, 187-192. Hayward, M.M.; Roth, R.M.; Duffy, K.J.; Dalko, P.I.; Stevens, K.L.; Guo, J.; Kishi, Y. Angew. Chem. Int. Ed. Engl. 1998, 37, 192-196.
27. 10. Crimmins, M.T.; O'Mahony, R. J. Org Chem. 1990, 55, 5894-5900. Crimmins, M.T.; Washburn, D.G.; Katz, J.D.; Zawacki, F.J. Tetrahedron Lett. 1998, 39, 3439-3442.
28. 10. Crimmins, M.T.; O'Mahony, R. J. Org Chem. 1990, 55, 5894-5900. Crimmins, M.T.; Washburn, D.G.; Katz, J.D.; Zawacki, F.J. Tetrahedron Lett. 1998, 39, 3439-3442.
29. 13C NMR and IR spectra as well as satisfactory combustion analyses. Yields are for isolated, chromatographically homogeneous material.
30. 12. Crimmins, M. T.; Zawacki, F. J. Tetrahedron Lett. 1996, 36, 6499-6502.
31. 13. Brown, H.C.; Randad, R.S.; Bhat, K.S.; Zaidlewicz, M.; Racherla, U.S. J. Am. Chem. Soc. 1990, 112, 2389-2392.
32. 14. Crimmins, M.T.; Al-awar, R.S.; Vallin, I.M.; O'Mahony, R.; Hollis, W.G., Jr.; Bankaitis-Davis, D.M.; Lever, J.G. J. Am. Chem. Soc. 1996, 118, 7513-7528. Crimmins, M.T.; Bankaitis-Davis, D.M.; Hollis, W.G. J. Org. Chem. 1988, 53, 652-657.
33. 14. Crimmins, M.T.; Al-awar, R.S.; Vallin, I.M.; O'Mahony, R.; Hollis, W.G., Jr.; Bankaitis-Davis, D.M.; Lever, J.G. J. Am. Chem. Soc. 1996, 118, 7513-7528. Crimmins, M.T.; Bankaitis-Davis, D.M.; Hollis, W.G. J. Org. Chem. 1988, 53, 652-657.
34. 15. Perron, F.; Albizati, K.F. Chem. Rev. 1989, 89, 1617-1661. Deslongchamps, P.; "Stereoelectronic Effects in Organic Chemistry" Organic Chemistry Series, Vol. 1 Pergamon Press, Oxford, England, 1983.
35. 15. Perron, F.; Albizati, K.F. Chem. Rev. 1989, 89, 1617-1661. Deslongchamps, P.; "Stereoelectronic Effects in Organic Chemistry" Organic Chemistry Series, Vol. 1 Pergamon Press, Oxford, England, 1983.
36. 13a); 5.25 (dt, J = 17, 2 Hz, 1H); 5.80 (ddd, J = 17, 10, 4 Hz, 1H); 7.25-7.35 (m, 5H).