Macrocycles by ring-closing-metathesis, XI: Syntheses of (R)-(+)- lasiodiplodin, zeranol and truncated salicylihalamides

Tetrahedron

Volumn 55, Issue 27, 1999, Pages 8215-8230

  Fürstner, Alois ^a   Seidel, Günter ^a   Kindler, Nicole ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

LASIODIPLODIN; MACROCYCLIC COMPOUND; SALICYLIHALAMIDE DERIVATIVE; UNCLASSIFIED DRUG; ZERANOL;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL BINDING; CYTOTOXICITY; DRUG SYNTHESIS; GERMANY; PRIORITY JOURNAL;

EID: 0033516492     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00302-6     Document Type: Article

References (96)

1. For previous papers of this series see: (a) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942. (b) Fürstner, A.; Langemann, K. Synthesis 1997, 792. (c) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 7005. (d) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (e) Fürstner, A.; Müller, T. Synlett 1997, 1010. (f) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130. (g) Fürstner, A.; Koch, D.; Langemann, K.; Leitner, W.; Six, C. Angew. Chem. 1997, 109, 2562; Angew. Chem. Int. Ed. Engl. 1997, 36, 2466. (h) Fürstner, A.; Müller, T. J. Org. Chem. 1998, 63, 424. (i) Fürstner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun., 1998, 1315. (j) Fürstner, A.; Seidel, G. Angew. Chem., 1998, 110, 1758; Angew. Chem. Int. Ed. 1998, 37, 1734.
2. For previous papers of this series see: (a) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942. (b) Fürstner, A.; Langemann, K. Synthesis 1997, 792. (c) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 7005. (d) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (e) Fürstner, A.; Müller, T. Synlett 1997, 1010. (f) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130. (g) Fürstner, A.; Koch, D.; Langemann, K.; Leitner, W.; Six, C. Angew. Chem. 1997, 109, 2562; Angew. Chem. Int. Ed. Engl. 1997, 36, 2466. (h) Fürstner, A.; Müller, T. J. Org. Chem. 1998, 63, 424. (i) Fürstner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun., 1998, 1315. (j) Fürstner, A.; Seidel, G. Angew. Chem., 1998, 110, 1758; Angew. Chem. Int. Ed. 1998, 37, 1734.
3. For previous papers of this series see: (a) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942. (b) Fürstner, A.; Langemann, K. Synthesis 1997, 792. (c) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 7005. (d) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (e) Fürstner, A.; Müller, T. Synlett 1997, 1010. (f) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130. (g) Fürstner, A.; Koch, D.; Langemann, K.; Leitner, W.; Six, C. Angew. Chem. 1997, 109, 2562; Angew. Chem. Int. Ed. Engl. 1997, 36, 2466. (h) Fürstner, A.; Müller, T. J. Org. Chem. 1998, 63, 424. (i) Fürstner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun., 1998, 1315. (j) Fürstner, A.; Seidel, G. Angew. Chem., 1998, 110, 1758; Angew. Chem. Int. Ed. 1998, 37, 1734.
4. For previous papers of this series see: (a) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942. (b) Fürstner, A.; Langemann, K. Synthesis 1997, 792. (c) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 7005. (d) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (e) Fürstner, A.; Müller, T. Synlett 1997, 1010. (f) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130. (g) Fürstner, A.; Koch, D.; Langemann, K.; Leitner, W.; Six, C. Angew. Chem. 1997, 109, 2562; Angew. Chem. Int. Ed. Engl. 1997, 36, 2466. (h) Fürstner, A.; Müller, T. J. Org. Chem. 1998, 63, 424. (i) Fürstner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun., 1998, 1315. (j) Fürstner, A.; Seidel, G. Angew. Chem., 1998, 110, 1758; Angew. Chem. Int. Ed. 1998, 37, 1734.
5. For previous papers of this series see: (a) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942. (b) Fürstner, A.; Langemann, K. Synthesis 1997, 792. (c) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 7005. (d) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (e) Fürstner, A.; Müller, T. Synlett 1997, 1010. (f) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130. (g) Fürstner, A.; Koch, D.; Langemann, K.; Leitner, W.; Six, C. Angew. Chem. 1997, 109, 2562; Angew. Chem. Int. Ed. Engl. 1997, 36, 2466. (h) Fürstner, A.; Müller, T. J. Org. Chem. 1998, 63, 424. (i) Fürstner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun., 1998, 1315. (j) Fürstner, A.; Seidel, G. Angew. Chem., 1998, 110, 1758; Angew. Chem. Int. Ed. 1998, 37, 1734.
6. For previous papers of this series see: (a) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942. (b) Fürstner, A.; Langemann, K. Synthesis 1997, 792. (c) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 7005. (d) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (e) Fürstner, A.; Müller, T. Synlett 1997, 1010. (f) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130. (g) Fürstner, A.; Koch, D.; Langemann, K.; Leitner, W.; Six, C. Angew. Chem. 1997, 109, 2562; Angew. Chem. Int. Ed. Engl. 1997, 36, 2466. (h) Fürstner, A.; Müller, T. J. Org. Chem. 1998, 63, 424. (i) Fürstner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun., 1998, 1315. (j) Fürstner, A.; Seidel, G. Angew. Chem., 1998, 110, 1758; Angew. Chem. Int. Ed. 1998, 37, 1734.
7. For previous papers of this series see: (a) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942. (b) Fürstner, A.; Langemann, K. Synthesis 1997, 792. (c) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 7005. (d) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (e) Fürstner, A.; Müller, T. Synlett 1997, 1010. (f) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130. (g) Fürstner, A.; Koch, D.; Langemann, K.; Leitner, W.; Six, C. Angew. Chem. 1997, 109, 2562; Angew. Chem. Int. Ed. Engl. 1997, 36, 2466. (h) Fürstner, A.; Müller, T. J. Org. Chem. 1998, 63, 424. (i) Fürstner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun., 1998, 1315. (j) Fürstner, A.; Seidel, G. Angew. Chem., 1998, 110, 1758; Angew. Chem. Int. Ed. 1998, 37, 1734.
8. For previous papers of this series see: (a) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942. (b) Fürstner, A.; Langemann, K. Synthesis 1997, 792. (c) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 7005. (d) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (e) Fürstner, A.; Müller, T. Synlett 1997, 1010. (f) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130. (g) Fürstner, A.; Koch, D.; Langemann, K.; Leitner, W.; Six, C. Angew. Chem. 1997, 109, 2562; Angew. Chem. Int. Ed. Engl. 1997, 36, 2466. (h) Fürstner, A.; Müller, T. J. Org. Chem. 1998, 63, 424. (i) Fürstner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun., 1998, 1315. (j) Fürstner, A.; Seidel, G. Angew. Chem., 1998, 110, 1758; Angew. Chem. Int. Ed. 1998, 37, 1734.
9. For previous papers of this series see: (a) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942. (b) Fürstner, A.; Langemann, K. Synthesis 1997, 792. (c) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 7005. (d) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (e) Fürstner, A.; Müller, T. Synlett 1997, 1010. (f) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130. (g) Fürstner, A.; Koch, D.; Langemann, K.; Leitner, W.; Six, C. Angew. Chem. 1997, 109, 2562; Angew. Chem. Int. Ed. Engl. 1997, 36, 2466. (h) Fürstner, A.; Müller, T. J. Org. Chem. 1998, 63, 424. (i) Fürstner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun., 1998, 1315. (j) Fürstner, A.; Seidel, G. Angew. Chem., 1998, 110, 1758; Angew. Chem. Int. Ed. 1998, 37, 1734.
10. For previous papers of this series see: (a) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942. (b) Fürstner, A.; Langemann, K. Synthesis 1997, 792. (c) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 7005. (d) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (e) Fürstner, A.; Müller, T. Synlett 1997, 1010. (f) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130. (g) Fürstner, A.; Koch, D.; Langemann, K.; Leitner, W.; Six, C. Angew. Chem. 1997, 109, 2562; Angew. Chem. Int. Ed. Engl. 1997, 36, 2466. (h) Fürstner, A.; Müller, T. J. Org. Chem. 1998, 63, 424. (i) Fürstner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun., 1998, 1315. (j) Fürstner, A.; Seidel, G. Angew. Chem., 1998, 110, 1758; Angew. Chem. Int. Ed. 1998, 37, 1734.
11. For previous papers of this series see: (a) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942. (b) Fürstner, A.; Langemann, K. Synthesis 1997, 792. (c) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 7005. (d) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (e) Fürstner, A.; Müller, T. Synlett 1997, 1010. (f) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130. (g) Fürstner, A.; Koch, D.; Langemann, K.; Leitner, W.; Six, C. Angew. Chem. 1997, 109, 2562; Angew. Chem. Int. Ed. Engl. 1997, 36, 2466. (h) Fürstner, A.; Müller, T. J. Org. Chem. 1998, 63, 424. (i) Fürstner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun., 1998, 1315. (j) Fürstner, A.; Seidel, G. Angew. Chem., 1998, 110, 1758; Angew. Chem. Int. Ed. 1998, 37, 1734.
12. For previous papers of this series see: (a) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942. (b) Fürstner, A.; Langemann, K. Synthesis 1997, 792. (c) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 7005. (d) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (e) Fürstner, A.; Müller, T. Synlett 1997, 1010. (f) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130. (g) Fürstner, A.; Koch, D.; Langemann, K.; Leitner, W.; Six, C. Angew. Chem. 1997, 109, 2562; Angew. Chem. Int. Ed. Engl. 1997, 36, 2466. (h) Fürstner, A.; Müller, T. J. Org. Chem. 1998, 63, 424. (i) Fürstner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun., 1998, 1315. (j) Fürstner, A.; Seidel, G. Angew. Chem., 1998, 110, 1758; Angew. Chem. Int. Ed. 1998, 37, 1734.
13. For recent reviews on RCM see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Fürstner, A. Top. Catal. 1997, 4, 285. (c) Schuster, M.; Blechert, S. Angew. Chem. Int. Ed. Engl. 1997, 36, 2036. (d) Fürstner, A. (Ed.), Top. Organomet. Chem., 1998, Vol. 1, Springer, Berlin.
14. For recent reviews on RCM see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Fürstner, A. Top. Catal. 1997, 4, 285. (c) Schuster, M.; Blechert, S. Angew. Chem. Int. Ed. Engl. 1997, 36, 2036. (d) Fürstner, A. (Ed.), Top. Organomet. Chem., 1998, Vol. 1, Springer, Berlin.
15. For recent reviews on RCM see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Fürstner, A. Top. Catal. 1997, 4, 285. (c) Schuster, M.; Blechert, S. Angew. Chem. Int. Ed. Engl. 1997, 36, 2036. (d) Fürstner, A. (Ed.), Top. Organomet. Chem., 1998, Vol. 1, Springer, Berlin.
16. For recent reviews on RCM see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Fürstner, A. Top. Catal. 1997, 4, 285. (c) Schuster, M.; Blechert, S. Angew. Chem. Int. Ed. Engl. 1997, 36, 2036. (d) Fürstner, A. (Ed.), Top. Organomet. Chem., 1998, Vol. 1, Springer, Berlin.
17. See the following for further leading references on the synthesis of macrocyclic natural products via RCM: (a) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (b) Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. 1997, 109, 170. (c) Nicolaou, K.C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem. 1996, 108, 2554. (d) Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. 1997, 109, 543. (e) Bertinato, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (f) Xu, Z.; Johannes, C. W.; Houri, A. F.; La, D. S.; Cogan, D. A.; Hofilena, G. E.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 10302. (g) Martin, S. F.; Liao, Y.; Chen, H.-J.; Pätzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 6005. (h) Ghosh, A. K.; Hussain, K. A. Tetrahedron Lett. 1998, 1881. (i) Magnier, E.; Langlois, Y. Tetrahedron Lett. 1998, 837 and references cited therein.
18. See the following for further leading references on the synthesis of macrocyclic natural products via RCM: (a) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (b) Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. 1997, 109, 170. (c) Nicolaou, K.C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem. 1996, 108, 2554. (d) Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. 1997, 109, 543. (e) Bertinato, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (f) Xu, Z.; Johannes, C. W.; Houri, A. F.; La, D. S.; Cogan, D. A.; Hofilena, G. E.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 10302. (g) Martin, S. F.; Liao, Y.; Chen, H.-J.; Pätzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 6005. (h) Ghosh, A. K.; Hussain, K. A. Tetrahedron Lett. 1998, 1881. (i) Magnier, E.; Langlois, Y. Tetrahedron Lett. 1998, 837 and references cited therein.
19. See the following for further leading references on the synthesis of macrocyclic natural products via RCM: (a) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (b) Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. 1997, 109, 170. (c) Nicolaou, K.C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem. 1996, 108, 2554. (d) Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. 1997, 109, 543. (e) Bertinato, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (f) Xu, Z.; Johannes, C. W.; Houri, A. F.; La, D. S.; Cogan, D. A.; Hofilena, G. E.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 10302. (g) Martin, S. F.; Liao, Y.; Chen, H.-J.; Pätzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 6005. (h) Ghosh, A. K.; Hussain, K. A. Tetrahedron Lett. 1998, 1881. (i) Magnier, E.; Langlois, Y. Tetrahedron Lett. 1998, 837 and references cited therein.
20. See the following for further leading references on the synthesis of macrocyclic natural products via RCM: (a) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (b) Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. 1997, 109, 170. (c) Nicolaou, K.C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem. 1996, 108, 2554. (d) Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. 1997, 109, 543. (e) Bertinato, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (f) Xu, Z.; Johannes, C. W.; Houri, A. F.; La, D. S.; Cogan, D. A.; Hofilena, G. E.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 10302. (g) Martin, S. F.; Liao, Y.; Chen, H.-J.; Pätzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 6005. (h) Ghosh, A. K.; Hussain, K. A. Tetrahedron Lett. 1998, 1881. (i) Magnier, E.; Langlois, Y. Tetrahedron Lett. 1998, 837 and references cited therein.
21. See the following for further leading references on the synthesis of macrocyclic natural products via RCM: (a) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (b) Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. 1997, 109, 170. (c) Nicolaou, K.C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem. 1996, 108, 2554. (d) Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. 1997, 109, 543. (e) Bertinato, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (f) Xu, Z.; Johannes, C. W.; Houri, A. F.; La, D. S.; Cogan, D. A.; Hofilena, G. E.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 10302. (g) Martin, S. F.; Liao, Y.; Chen, H.-J.; Pätzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 6005. (h) Ghosh, A. K.; Hussain, K. A. Tetrahedron Lett. 1998, 1881. (i) Magnier, E.; Langlois, Y. Tetrahedron Lett. 1998, 837 and references cited therein.
22. See the following for further leading references on the synthesis of macrocyclic natural products via RCM: (a) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (b) Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. 1997, 109, 170. (c) Nicolaou, K.C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem. 1996, 108, 2554. (d) Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. 1997, 109, 543. (e) Bertinato, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (f) Xu, Z.; Johannes, C. W.; Houri, A. F.; La, D. S.; Cogan, D. A.; Hofilena, G. E.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 10302. (g) Martin, S. F.; Liao, Y.; Chen, H.-J.; Pätzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 6005. (h) Ghosh, A. K.; Hussain, K. A. Tetrahedron Lett. 1998, 1881. (i) Magnier, E.; Langlois, Y. Tetrahedron Lett. 1998, 837 and references cited therein.
23. See the following for further leading references on the synthesis of macrocyclic natural products via RCM: (a) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (b) Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. 1997, 109, 170. (c) Nicolaou, K.C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem. 1996, 108, 2554. (d) Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. 1997, 109, 543. (e) Bertinato, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (f) Xu, Z.; Johannes, C. W.; Houri, A. F.; La, D. S.; Cogan, D. A.; Hofilena, G. E.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 10302. (g) Martin, S. F.; Liao, Y.; Chen, H.-J.; Pätzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 6005. (h) Ghosh, A. K.; Hussain, K. A. Tetrahedron Lett. 1998, 1881. (i) Magnier, E.; Langlois, Y. Tetrahedron Lett. 1998, 837 and references cited therein.
24. See the following for further leading references on the synthesis of macrocyclic natural products via RCM: (a) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (b) Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. 1997, 109, 170. (c) Nicolaou, K.C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem. 1996, 108, 2554. (d) Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. 1997, 109, 543. (e) Bertinato, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (f) Xu, Z.; Johannes, C. W.; Houri, A. F.; La, D. S.; Cogan, D. A.; Hofilena, G. E.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 10302. (g) Martin, S. F.; Liao, Y.; Chen, H.-J.; Pätzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 6005. (h) Ghosh, A. K.; Hussain, K. A. Tetrahedron Lett. 1998, 1881. (i) Magnier, E.; Langlois, Y. Tetrahedron Lett. 1998, 837 and references cited therein.
25. See the following for further leading references on the synthesis of macrocyclic natural products via RCM: (a) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (b) Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. 1997, 109, 170. (c) Nicolaou, K.C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem. 1996, 108, 2554. (d) Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. 1997, 109, 543. (e) Bertinato, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (f) Xu, Z.; Johannes, C. W.; Houri, A. F.; La, D. S.; Cogan, D. A.; Hofilena, G. E.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 10302. (g) Martin, S. F.; Liao, Y.; Chen, H.-J.; Pätzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 6005. (h) Ghosh, A. K.; Hussain, K. A. Tetrahedron Lett. 1998, 1881. (i) Magnier, E.; Langlois, Y. Tetrahedron Lett. 1998, 837 and references cited therein.
26. Leading references on other orsellinic acid type macrolides: (a) Monocillin: Lett, R.; Lampilas, M.; Tischkowsky, I. in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products (Lukacs, G., Ed.), Springer, Berlin, Vol. 2, 1993, p. 99. (b) Resorcylide: Oyama, H.; Sassa, T.; Ikeda, M. Agric. Biol. Chem. 1978, 42, 2407-2409. (c) Zearalenone: cf. ref. [16-18].
27. Leading references on other orsellinic acid type macrolides: (a) Monocillin: Lett, R.; Lampilas, M.; Tischkowsky, I. in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products (Lukacs, G., Ed.), Springer, Berlin, Vol. 2, 1993, p. 99. (b) Resorcylide: Oyama, H.; Sassa, T.; Ikeda, M. Agric. Biol. Chem. 1978, 42, 2407-2409. (c) Zearalenone: cf. ref. [16-18].
28. Leading references on other orsellinic acid type macrolides: (a) Monocillin: Lett, R.; Lampilas, M.; Tischkowsky, I. in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products (Lukacs, G., Ed.), Springer, Berlin, Vol. 2, 1993, p. 99. (b) Resorcylide: Oyama, H.; Sassa, T.; Ikeda, M. Agric. Biol. Chem. 1978, 42, 2407-2409. (c) Zearalenone: cf. ref. [16-18].
29. (a) Aldridge, D. C.; Galt, S.; Giles, D.; Turner, W. B. J. Chem. Soc. (C) 1971, 1623. (b) Cambie, R. C.; Lal, A. R.; Rutledge, P. S.; Woodgate, P. D. Phytochemistry 1991, 30, 287. (c) Lee, K.-H.; Hayashi, N.; Okano, M.; Hall, I. H.; Wu, R.-Y.; McPhail, A. T. Phytochemistry 1982, 21, 1119. (d) Xin-Seng, Y.; Ebizuka, Y.; Noguchi, H.; Kiuchi, F.; Iitaka, Y.; Sankawa, U.; Seto, H. Tetrahedron Lett. 1983, 2407. (e) For the isolation of new lasiodiplodin derivatives see: Matsuura, H.; Nakamori, K.; Omer, E. A.; Hatakeyama, C.; Yoshihara, T.; Ichihara, A. Phytochemistry 1998, 49, 579. (f) Barrow, C. J. J. Nat. Prod. 1997, 60, 1023.
30. (a) Aldridge, D. C.; Galt, S.; Giles, D.; Turner, W. B. J. Chem. Soc. (C) 1971, 1623. (b) Cambie, R. C.; Lal, A. R.; Rutledge, P. S.; Woodgate, P. D. Phytochemistry 1991, 30, 287. (c) Lee, K.-H.; Hayashi, N.; Okano, M.; Hall, I. H.; Wu, R.-Y.; McPhail, A. T. Phytochemistry 1982, 21, 1119. (d) Xin-Seng, Y.; Ebizuka, Y.; Noguchi, H.; Kiuchi, F.; Iitaka, Y.; Sankawa, U.; Seto, H. Tetrahedron Lett. 1983, 2407. (e) For the isolation of new lasiodiplodin derivatives see: Matsuura, H.; Nakamori, K.; Omer, E. A.; Hatakeyama, C.; Yoshihara, T.; Ichihara, A. Phytochemistry 1998, 49, 579. (f) Barrow, C. J. J. Nat. Prod. 1997, 60, 1023.
31. (a) Aldridge, D. C.; Galt, S.; Giles, D.; Turner, W. B. J. Chem. Soc. (C) 1971, 1623. (b) Cambie, R. C.; Lal, A. R.; Rutledge, P. S.; Woodgate, P. D. Phytochemistry 1991, 30, 287. (c) Lee, K.-H.; Hayashi, N.; Okano, M.; Hall, I. H.; Wu, R.-Y.; McPhail, A. T. Phytochemistry 1982, 21, 1119. (d) Xin-Seng, Y.; Ebizuka, Y.; Noguchi, H.; Kiuchi, F.; Iitaka, Y.; Sankawa, U.; Seto, H. Tetrahedron Lett. 1983, 2407. (e) For the isolation of new lasiodiplodin derivatives see: Matsuura, H.; Nakamori, K.; Omer, E. A.; Hatakeyama, C.; Yoshihara, T.; Ichihara, A. Phytochemistry 1998, 49, 579. (f) Barrow, C. J. J. Nat. Prod. 1997, 60, 1023.
32. (a) Aldridge, D. C.; Galt, S.; Giles, D.; Turner, W. B. J. Chem. Soc. (C) 1971, 1623. (b) Cambie, R. C.; Lal, A. R.; Rutledge, P. S.; Woodgate, P. D. Phytochemistry 1991, 30, 287. (c) Lee, K.-H.; Hayashi, N.; Okano, M.; Hall, I. H.; Wu, R.-Y.; McPhail, A. T. Phytochemistry 1982, 21, 1119. (d) Xin-Seng, Y.; Ebizuka, Y.; Noguchi, H.; Kiuchi, F.; Iitaka, Y.; Sankawa, U.; Seto, H. Tetrahedron Lett. 1983, 2407. (e) For the isolation of new lasiodiplodin derivatives see: Matsuura, H.; Nakamori, K.; Omer, E. A.; Hatakeyama, C.; Yoshihara, T.; Ichihara, A. Phytochemistry 1998, 49, 579. (f) Barrow, C. J. J. Nat. Prod. 1997, 60, 1023.
33. (a) Aldridge, D. C.; Galt, S.; Giles, D.; Turner, W. B. J. Chem. Soc. (C) 1971, 1623. (b) Cambie, R. C.; Lal, A. R.; Rutledge, P. S.; Woodgate, P. D. Phytochemistry 1991, 30, 287. (c) Lee, K.-H.; Hayashi, N.; Okano, M.; Hall, I. H.; Wu, R.-Y.; McPhail, A. T. Phytochemistry 1982, 21, 1119. (d) Xin-Seng, Y.; Ebizuka, Y.; Noguchi, H.; Kiuchi, F.; Iitaka, Y.; Sankawa, U.; Seto, H. Tetrahedron Lett. 1983, 2407. (e) For the isolation of new lasiodiplodin derivatives see: Matsuura, H.; Nakamori, K.; Omer, E. A.; Hatakeyama, C.; Yoshihara, T.; Ichihara, A. Phytochemistry 1998, 49, 579. (f) Barrow, C. J. J. Nat. Prod. 1997, 60, 1023.
34. (a) Aldridge, D. C.; Galt, S.; Giles, D.; Turner, W. B. J. Chem. Soc. (C) 1971, 1623. (b) Cambie, R. C.; Lal, A. R.; Rutledge, P. S.; Woodgate, P. D. Phytochemistry 1991, 30, 287. (c) Lee, K.-H.; Hayashi, N.; Okano, M.; Hall, I. H.; Wu, R.-Y.; McPhail, A. T. Phytochemistry 1982, 21, 1119. (d) Xin-Seng, Y.; Ebizuka, Y.; Noguchi, H.; Kiuchi, F.; Iitaka, Y.; Sankawa, U.; Seto, H. Tetrahedron Lett. 1983, 2407. (e) For the isolation of new lasiodiplodin derivatives see: Matsuura, H.; Nakamori, K.; Omer, E. A.; Hatakeyama, C.; Yoshihara, T.; Ichihara, A. Phytochemistry 1998, 49, 579. (f) Barrow, C. J. J. Nat. Prod. 1997, 60, 1023.
35. Previous syntheses of lasiodiplodin: (a) Gerlach, H.; Thalmann, A. Helv. Chim. Acta 1977, 60, 2866. (b) Danishefsky, S.; Etheredge, S. J. J. Org. Chem. 1979, 44, 4716. (c) Takahashi, T.; Kasuga, K.; Tsuji, J. Tetrahedron Lett. 1978, 4917. (d) Braun, M.; Mahler, U.; Houben, S. Liebigs Ann. 1990, 513. (e) Jones, G. B.; Huber, R. S. Synlett 1993, 367. (f) Fink, M.; Gaier, H.; Gerlach, H. Helv. Chim. Acta 1982, 65, 2563. (g) Solladié, G.; Rubio, A.; Carreño, M. C.; Garcia Ruano, J. L. Tetrahedron: Asymmetry 1990, 1, 187. (h) Bracher, F.; Schulte, B. J. Chem. Soc. Perkin Trans. 1 1996, 2619.
36. Previous syntheses of lasiodiplodin: (a) Gerlach, H.; Thalmann, A. Helv. Chim. Acta 1977, 60, 2866. (b) Danishefsky, S.; Etheredge, S. J. J. Org. Chem. 1979, 44, 4716. (c) Takahashi, T.; Kasuga, K.; Tsuji, J. Tetrahedron Lett. 1978, 4917. (d) Braun, M.; Mahler, U.; Houben, S. Liebigs Ann. 1990, 513. (e) Jones, G. B.; Huber, R. S. Synlett 1993, 367. (f) Fink, M.; Gaier, H.; Gerlach, H. Helv. Chim. Acta 1982, 65, 2563. (g) Solladié, G.; Rubio, A.; Carreño, M. C.; Garcia Ruano, J. L. Tetrahedron: Asymmetry 1990, 1, 187. (h) Bracher, F.; Schulte, B. J. Chem. Soc. Perkin Trans. 1 1996, 2619.
37. Previous syntheses of lasiodiplodin: (a) Gerlach, H.; Thalmann, A. Helv. Chim. Acta 1977, 60, 2866. (b) Danishefsky, S.; Etheredge, S. J. J. Org. Chem. 1979, 44, 4716. (c) Takahashi, T.; Kasuga, K.; Tsuji, J. Tetrahedron Lett. 1978, 4917. (d) Braun, M.; Mahler, U.; Houben, S. Liebigs Ann. 1990, 513. (e) Jones, G. B.; Huber, R. S. Synlett 1993, 367. (f) Fink, M.; Gaier, H.; Gerlach, H. Helv. Chim. Acta 1982, 65, 2563. (g) Solladié, G.; Rubio, A.; Carreño, M. C.; Garcia Ruano, J. L. Tetrahedron: Asymmetry 1990, 1, 187. (h) Bracher, F.; Schulte, B. J. Chem. Soc. Perkin Trans. 1 1996, 2619.
38. Previous syntheses of lasiodiplodin: (a) Gerlach, H.; Thalmann, A. Helv. Chim. Acta 1977, 60, 2866. (b) Danishefsky, S.; Etheredge, S. J. J. Org. Chem. 1979, 44, 4716. (c) Takahashi, T.; Kasuga, K.; Tsuji, J. Tetrahedron Lett. 1978, 4917. (d) Braun, M.; Mahler, U.; Houben, S. Liebigs Ann. 1990, 513. (e) Jones, G. B.; Huber, R. S. Synlett 1993, 367. (f) Fink, M.; Gaier, H.; Gerlach, H. Helv. Chim. Acta 1982, 65, 2563. (g) Solladié, G.; Rubio, A.; Carreño, M. C.; Garcia Ruano, J. L. Tetrahedron: Asymmetry 1990, 1, 187. (h) Bracher, F.; Schulte, B. J. Chem. Soc. Perkin Trans. 1 1996, 2619.
39. Previous syntheses of lasiodiplodin: (a) Gerlach, H.; Thalmann, A. Helv. Chim. Acta 1977, 60, 2866. (b) Danishefsky, S.; Etheredge, S. J. J. Org. Chem. 1979, 44, 4716. (c) Takahashi, T.; Kasuga, K.; Tsuji, J. Tetrahedron Lett. 1978, 4917. (d) Braun, M.; Mahler, U.; Houben, S. Liebigs Ann. 1990, 513. (e) Jones, G. B.; Huber, R. S. Synlett 1993, 367. (f) Fink, M.; Gaier, H.; Gerlach, H. Helv. Chim. Acta 1982, 65, 2563. (g) Solladié, G.; Rubio, A.; Carreño, M. C.; Garcia Ruano, J. L. Tetrahedron: Asymmetry 1990, 1, 187. (h) Bracher, F.; Schulte, B. J. Chem. Soc. Perkin Trans. 1 1996, 2619.
40. Previous syntheses of lasiodiplodin: (a) Gerlach, H.; Thalmann, A. Helv. Chim. Acta 1977, 60, 2866. (b) Danishefsky, S.; Etheredge, S. J. J. Org. Chem. 1979, 44, 4716. (c) Takahashi, T.; Kasuga, K.; Tsuji, J. Tetrahedron Lett. 1978, 4917. (d) Braun, M.; Mahler, U.; Houben, S. Liebigs Ann. 1990, 513. (e) Jones, G. B.; Huber, R. S. Synlett 1993, 367. (f) Fink, M.; Gaier, H.; Gerlach, H. Helv. Chim. Acta 1982, 65, 2563. (g) Solladié, G.; Rubio, A.; Carreño, M. C.; Garcia Ruano, J. L. Tetrahedron: Asymmetry 1990, 1, 187. (h) Bracher, F.; Schulte, B. J. Chem. Soc. Perkin Trans. 1 1996, 2619.
41. Previous syntheses of lasiodiplodin: (a) Gerlach, H.; Thalmann, A. Helv. Chim. Acta 1977, 60, 2866. (b) Danishefsky, S.; Etheredge, S. J. J. Org. Chem. 1979, 44, 4716. (c) Takahashi, T.; Kasuga, K.; Tsuji, J. Tetrahedron Lett. 1978, 4917. (d) Braun, M.; Mahler, U.; Houben, S. Liebigs Ann. 1990, 513. (e) Jones, G. B.; Huber, R. S. Synlett 1993, 367. (f) Fink, M.; Gaier, H.; Gerlach, H. Helv. Chim. Acta 1982, 65, 2563. (g) Solladié, G.; Rubio, A.; Carreño, M. C.; Garcia Ruano, J. L. Tetrahedron: Asymmetry 1990, 1, 187. (h) Bracher, F.; Schulte, B. J. Chem. Soc. Perkin Trans. 1 1996, 2619.
42. Previous syntheses of lasiodiplodin: (a) Gerlach, H.; Thalmann, A. Helv. Chim. Acta 1977, 60, 2866. (b) Danishefsky, S.; Etheredge, S. J. J. Org. Chem. 1979, 44, 4716. (c) Takahashi, T.; Kasuga, K.; Tsuji, J. Tetrahedron Lett. 1978, 4917. (d) Braun, M.; Mahler, U.; Houben, S. Liebigs Ann. 1990, 513. (e) Jones, G. B.; Huber, R. S. Synlett 1993, 367. (f) Fink, M.; Gaier, H.; Gerlach, H. Helv. Chim. Acta 1982, 65, 2563. (g) Solladié, G.; Rubio, A.; Carreño, M. C.; Garcia Ruano, J. L. Tetrahedron: Asymmetry 1990, 1, 187. (h) Bracher, F.; Schulte, B. J. Chem. Soc. Perkin Trans. 1 1996, 2619.
43. Maillard, J.; Vincent, M.; Delaunay, P; Fumeron, B. Bull. Soc. Chim. Fr. 1966, 2520.
44. Now readily available by the excellent resolution method of Jacobsen et al., cf.: Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936.
45. See also: (a) Fürstner, A.; Konetzki, I. J. Org. Chem. 1998, 63, 3072. (b) Fürstner, A.; Konetzki, I. Tetrahedron 1996, 52, 15071.
46. See also: (a) Fürstner, A.; Konetzki, I. J. Org. Chem. 1998, 63, 3072. (b) Fürstner, A.; Konetzki, I. Tetrahedron 1996, 52, 15071.
47. Mitsunobu, O. Synthesis 1981, 1.
48. (a) Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585. Reviews: (b) Stille, J. K. Angew. Chem. 1986, 98, 504. (c) Ritter, K. Synthesis 1993, 735.
49. (a) Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585. Reviews: (b) Stille, J. K. Angew. Chem. 1986, 98, 504. (c) Ritter, K. Synthesis 1993, 735.
50. (a) Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585. Reviews: (b) Stille, J. K. Angew. Chem. 1986, 98, 504. (c) Ritter, K. Synthesis 1993, 735.
51. (a) Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 9858. (b) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem. Int. Ed. Engl. 1995, 34, 2039. (c) Dias, E.L.; Nguyen, S.T.; Grubbs, R.H. J. Am. Chem. Soc. 1997, 119, 3887.
52. (a) Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 9858. (b) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem. Int. Ed. Engl. 1995, 34, 2039. (c) Dias, E.L.; Nguyen, S.T.; Grubbs, R.H. J. Am. Chem. Soc. 1997, 119, 3887.
53. (a) Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 9858. (b) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem. Int. Ed. Engl. 1995, 34, 2039. (c) Dias, E.L.; Nguyen, S.T.; Grubbs, R.H. J. Am. Chem. Soc. 1997, 119, 3887.
54. Erickson, K. L.; Beutler, J. A.; Cardellina, J. H.; Boyd, M. R. J. Org. Chem. 1997, 62, 8188.
55. Some selected in-vitro cytotoxicity data of compound 16: (Table Presented)
56. For studies on other anti-tumor agents from this laboratory see: (a) Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1998, 720, 2817. (b) Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1997, 119, 2944. (c) Fürstner, A.; Seidel, G. J. Org. Chem. 1997, 62, 2332. (d) Fürstner, A.; Nikolakis, K. Liebigs Ann. 1996, 2107. (e) Fürstner, A.; Jumbam, D. N., Seidel, G. Chem. Ber. 1994, 127, 1125. (f) Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305.
57. For studies on other anti-tumor agents from this laboratory see: (a) Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1998, 720, 2817. (b) Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1997, 119, 2944. (c) Fürstner, A.; Seidel, G. J. Org. Chem. 1997, 62, 2332. (d) Fürstner, A.; Nikolakis, K. Liebigs Ann. 1996, 2107. (e) Fürstner, A.; Jumbam, D. N., Seidel, G. Chem. Ber. 1994, 127, 1125. (f) Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305.
58. For studies on other anti-tumor agents from this laboratory see: (a) Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1998, 720, 2817. (b) Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1997, 119, 2944. (c) Fürstner, A.; Seidel, G. J. Org. Chem. 1997, 62, 2332. (d) Fürstner, A.; Nikolakis, K. Liebigs Ann. 1996, 2107. (e) Fürstner, A.; Jumbam, D. N., Seidel, G. Chem. Ber. 1994, 127, 1125. (f) Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305.
59. For studies on other anti-tumor agents from this laboratory see: (a) Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1998, 720, 2817. (b) Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1997, 119, 2944. (c) Fürstner, A.; Seidel, G. J. Org. Chem. 1997, 62, 2332. (d) Fürstner, A.; Nikolakis, K. Liebigs Ann. 1996, 2107. (e) Fürstner, A.; Jumbam, D. N., Seidel, G. Chem. Ber. 1994, 127, 1125. (f) Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305.
60. For studies on other anti-tumor agents from this laboratory see: (a) Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1998, 720, 2817. (b) Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1997, 119, 2944. (c) Fürstner, A.; Seidel, G. J. Org. Chem. 1997, 62, 2332. (d) Fürstner, A.; Nikolakis, K. Liebigs Ann. 1996, 2107. (e) Fürstner, A.; Jumbam, D. N., Seidel, G. Chem. Ber. 1994, 127, 1125. (f) Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305.
61. For studies on other anti-tumor agents from this laboratory see: (a) Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1998, 720, 2817. (b) Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1997, 119, 2944. (c) Fürstner, A.; Seidel, G. J. Org. Chem. 1997, 62, 2332. (d) Fürstner, A.; Nikolakis, K. Liebigs Ann. 1996, 2107. (e) Fürstner, A.; Jumbam, D. N., Seidel, G. Chem. Ber. 1994, 127, 1125. (f) Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305.
62. Reviews: (a) Betina, V. Zearalenone and Its Derivatives in Mycotoxins: Chemical, Biological and Environmental Aspects, Elsevier, Amsterdam, 1989. (b) Shipchandler, M. T. Heterocycles 1975, 3, 471. Isolation and Structure: (c) Stob, M.; Baldwin, R. S.; Tuite, J.; Andrews, F. N.; Gillette, K. G. Nature 1962, 196, 1318. (d) Urry, W. H.; Wehrmeister, H. L.; Hodge, E. B.; Hidy, P. H. Tetrahedron Lett. 1966, 3109. (e) Cordier, C.; Gruselle, M.; Jaouen, G.; Hughes, D. W.; McGlinchey, M. J. Magn. Res. Chem. 1990, 28, 835.
63. Reviews: (a) Betina, V. Zearalenone and Its Derivatives in Mycotoxins: Chemical, Biological and Environmental Aspects, Elsevier, Amsterdam, 1989. (b) Shipchandler, M. T. Heterocycles 1975, 3, 471. Isolation and Structure: (c) Stob, M.; Baldwin, R. S.; Tuite, J.; Andrews, F. N.; Gillette, K. G. Nature 1962, 196, 1318. (d) Urry, W. H.; Wehrmeister, H. L.; Hodge, E. B.; Hidy, P. H. Tetrahedron Lett. 1966, 3109. (e) Cordier, C.; Gruselle, M.; Jaouen, G.; Hughes, D. W.; McGlinchey, M. J. Magn. Res. Chem. 1990, 28, 835.
64. Reviews: (a) Betina, V. Zearalenone and Its Derivatives in Mycotoxins: Chemical, Biological and Environmental Aspects, Elsevier, Amsterdam, 1989. (b) Shipchandler, M. T. Heterocycles 1975, 3, 471. Isolation and Structure: (c) Stob, M.; Baldwin, R. S.; Tuite, J.; Andrews, F. N.; Gillette, K. G. Nature 1962, 196, 1318. (d) Urry, W. H.; Wehrmeister, H. L.; Hodge, E. B.; Hidy, P. H. Tetrahedron Lett. 1966, 3109. (e) Cordier, C.; Gruselle, M.; Jaouen, G.; Hughes, D. W.; McGlinchey, M. J. Magn. Res. Chem. 1990, 28, 835.
65. Reviews: (a) Betina, V. Zearalenone and Its Derivatives in Mycotoxins: Chemical, Biological and Environmental Aspects, Elsevier, Amsterdam, 1989. (b) Shipchandler, M. T. Heterocycles 1975, 3, 471. Isolation and Structure: (c) Stob, M.; Baldwin, R. S.; Tuite, J.; Andrews, F. N.; Gillette, K. G. Nature 1962, 196, 1318. (d) Urry, W. H.; Wehrmeister, H. L.; Hodge, E. B.; Hidy, P. H. Tetrahedron Lett. 1966, 3109. (e) Cordier, C.; Gruselle, M.; Jaouen, G.; Hughes, D. W.; McGlinchey, M. J. Magn. Res. Chem. 1990, 28, 835.
66. Reviews: (a) Betina, V. Zearalenone and Its Derivatives in Mycotoxins: Chemical, Biological and Environmental Aspects, Elsevier, Amsterdam, 1989. (b) Shipchandler, M. T. Heterocycles 1975, 3, 471. Isolation and Structure: (c) Stob, M.; Baldwin, R. S.; Tuite, J.; Andrews, F. N.; Gillette, K. G. Nature 1962, 196, 1318. (d) Urry, W. H.; Wehrmeister, H. L.; Hodge, E. B.; Hidy, P. H. Tetrahedron Lett. 1966, 3109. (e) Cordier, C.; Gruselle, M.; Jaouen, G.; Hughes, D. W.; McGlinchey, M. J. Magn. Res. Chem. 1990, 28, 835.
67. (a) US Pat. 3,239345 (CA 1967, 66: 2345t); US Pat 3,487982 (CA 1972, 77: 164537w); Ger. Offen. 211618 (CA 1972, 76: 25120w); Ger. Offen. 205644 (CA 1972, 76: 84551) to Commercial Solvents Corp. (b) For previous studies see: Snatzke, G.; Angeli, C.; Decorte, E.; Moimas, F.; Kojic-Prodic, B.; Ruzic-Toros, Z.; Sunjic V. Helv. Chim. Acta 1986, 69, 734. (c) Gelo, M.; Sunjic, V. Tetrahedron 1992, 48, 6511 and ref. cited.
68. (a) US Pat. 3,239345 (CA 1967, 66: 2345t); US Pat 3,487982 (CA 1972, 77: 164537w); Ger. Offen. 211618 (CA 1972, 76: 25120w); Ger. Offen. 205644 (CA 1972, 76: 84551) to Commercial Solvents Corp. (b) For previous studies see: Snatzke, G.; Angeli, C.; Decorte, E.; Moimas, F.; Kojic-Prodic, B.; Ruzic-Toros, Z.; Sunjic V. Helv. Chim. Acta 1986, 69, 734. (c) Gelo, M.; Sunjic, V. Tetrahedron 1992, 48, 6511 and ref. cited.
69. (a) US Pat. 3,239345 (CA 1967, 66: 2345t); US Pat 3,487982 (CA 1972, 77: 164537w); Ger. Offen. 211618 (CA 1972, 76: 25120w); Ger. Offen. 205644 (CA 1972, 76: 84551) to Commercial Solvents Corp. (b) For previous studies see: Snatzke, G.; Angeli, C.; Decorte, E.; Moimas, F.; Kojic-Prodic, B.; Ruzic-Toros, Z.; Sunjic V. Helv. Chim. Acta 1986, 69, 734. (c) Gelo, M.; Sunjic, V. Tetrahedron 1992, 48, 6511 and ref. cited.
70. For synthetic studies on the zearalenone family of macrolides see the following for leading references: (a) Keinan, E.; Sinha, S. C.; Sinha-Bagchi, A. J. Chem. Soc. Pertin 1 1991, 3333. (b) Hitchcock, S. A.; Pattenden, G. J. Chem. Soc. Perkin Trans. 1 1992, 1323. (c) Takahashi, T.; Nagashima, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1982, 23, 4361. (d) Takahashi, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1981, 22, 1363. (e) Kalivretenos, A.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883. (f) Rama Rao, A. V.; Deshmukh, M. N.; Sharma, G. V. M. Tetrahedron 1987, 43, 779. (g) Takahashi, T.; Kasuga, K.; Takahashi, M.; Tsuji, J. J. Am. Chem. Soc. 1979, 101, 5072. (h) Solladié, G.; Maestro, M. C.; Rubio, A.; Pedregal, C.; Carreno, M. C; Garcia Ruano, J. L. J. Org. Chem. 1991, 56, 2317. (i) Taub, D.; Girothra, N. N.; Hoffsommer, R. D.; Kuo, C. H.; Slates, H. L.; Weber, S.; Wendler, N. L. Tetrahedron 1968, 24, 2443. (j) Vlattas, I.; Harrison, I. T.; Tökes, L.; Fried, J. H.; Cross, A. D. J. Org. Chem. 1968, 33, 4176. (k) Windholz, T. B.; Brown, R. D. J. Org. Chem. 1972, 37, 1647. (l) Hurd, R. N.; Shah, D. H. J. Org. Chem. 1973, 38, 390. (m) Hurd, R. N.; Shah, D. H. J. Med. Chem. 1973, 16, 543. (n) Peters, C. A.; Hurd, R. N. J. Med. Chem. 1975, 18, 215. (o) Bass, R. J.; Banks, B. J.; Leeming, M. R. G.; Snarey, M. J. Chem. Soc. Perkin Trans. 1 1981, 124. (p) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem. 1998, 110, 2677.
71. For synthetic studies on the zearalenone family of macrolides see the following for leading references: (a) Keinan, E.; Sinha, S. C.; Sinha-Bagchi, A. J. Chem. Soc. Pertin 1 1991, 3333. (b) Hitchcock, S. A.; Pattenden, G. J. Chem. Soc. Perkin Trans. 1 1992, 1323. (c) Takahashi, T.; Nagashima, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1982, 23, 4361. (d) Takahashi, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1981, 22, 1363. (e) Kalivretenos, A.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883. (f) Rama Rao, A. V.; Deshmukh, M. N.; Sharma, G. V. M. Tetrahedron 1987, 43, 779. (g) Takahashi, T.; Kasuga, K.; Takahashi, M.; Tsuji, J. J. Am. Chem. Soc. 1979, 101, 5072. (h) Solladié, G.; Maestro, M. C.; Rubio, A.; Pedregal, C.; Carreno, M. C; Garcia Ruano, J. L. J. Org. Chem. 1991, 56, 2317. (i) Taub, D.; Girothra, N. N.; Hoffsommer, R. D.; Kuo, C. H.; Slates, H. L.; Weber, S.; Wendler, N. L. Tetrahedron 1968, 24, 2443. (j) Vlattas, I.; Harrison, I. T.; Tökes, L.; Fried, J. H.; Cross, A. D. J. Org. Chem. 1968, 33, 4176. (k) Windholz, T. B.; Brown, R. D. J. Org. Chem. 1972, 37, 1647. (l) Hurd, R. N.; Shah, D. H. J. Org. Chem. 1973, 38, 390. (m) Hurd, R. N.; Shah, D. H. J. Med. Chem. 1973, 16, 543. (n) Peters, C. A.; Hurd, R. N. J. Med. Chem. 1975, 18, 215. (o) Bass, R. J.; Banks, B. J.; Leeming, M. R. G.; Snarey, M. J. Chem. Soc. Perkin Trans. 1 1981, 124. (p) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem. 1998, 110, 2677.
72. For synthetic studies on the zearalenone family of macrolides see the following for leading references: (a) Keinan, E.; Sinha, S. C.; Sinha-Bagchi, A. J. Chem. Soc. Pertin 1 1991, 3333. (b) Hitchcock, S. A.; Pattenden, G. J. Chem. Soc. Perkin Trans. 1 1992, 1323. (c) Takahashi, T.; Nagashima, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1982, 23, 4361. (d) Takahashi, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1981, 22, 1363. (e) Kalivretenos, A.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883. (f) Rama Rao, A. V.; Deshmukh, M. N.; Sharma, G. V. M. Tetrahedron 1987, 43, 779. (g) Takahashi, T.; Kasuga, K.; Takahashi, M.; Tsuji, J. J. Am. Chem. Soc. 1979, 101, 5072. (h) Solladié, G.; Maestro, M. C.; Rubio, A.; Pedregal, C.; Carreno, M. C; Garcia Ruano, J. L. J. Org. Chem. 1991, 56, 2317. (i) Taub, D.; Girothra, N. N.; Hoffsommer, R. D.; Kuo, C. H.; Slates, H. L.; Weber, S.; Wendler, N. L. Tetrahedron 1968, 24, 2443. (j) Vlattas, I.; Harrison, I. T.; Tökes, L.; Fried, J. H.; Cross, A. D. J. Org. Chem. 1968, 33, 4176. (k) Windholz, T. B.; Brown, R. D. J. Org. Chem. 1972, 37, 1647. (l) Hurd, R. N.; Shah, D. H. J. Org. Chem. 1973, 38, 390. (m) Hurd, R. N.; Shah, D. H. J. Med. Chem. 1973, 16, 543. (n) Peters, C. A.; Hurd, R. N. J. Med. Chem. 1975, 18, 215. (o) Bass, R. J.; Banks, B. J.; Leeming, M. R. G.; Snarey, M. J. Chem. Soc. Perkin Trans. 1 1981, 124. (p) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem. 1998, 110, 2677.
73. For synthetic studies on the zearalenone family of macrolides see the following for leading references: (a) Keinan, E.; Sinha, S. C.; Sinha-Bagchi, A. J. Chem. Soc. Pertin 1 1991, 3333. (b) Hitchcock, S. A.; Pattenden, G. J. Chem. Soc. Perkin Trans. 1 1992, 1323. (c) Takahashi, T.; Nagashima, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1982, 23, 4361. (d) Takahashi, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1981, 22, 1363. (e) Kalivretenos, A.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883. (f) Rama Rao, A. V.; Deshmukh, M. N.; Sharma, G. V. M. Tetrahedron 1987, 43, 779. (g) Takahashi, T.; Kasuga, K.; Takahashi, M.; Tsuji, J. J. Am. Chem. Soc. 1979, 101, 5072. (h) Solladié, G.; Maestro, M. C.; Rubio, A.; Pedregal, C.; Carreno, M. C; Garcia Ruano, J. L. J. Org. Chem. 1991, 56, 2317. (i) Taub, D.; Girothra, N. N.; Hoffsommer, R. D.; Kuo, C. H.; Slates, H. L.; Weber, S.; Wendler, N. L. Tetrahedron 1968, 24, 2443. (j) Vlattas, I.; Harrison, I. T.; Tökes, L.; Fried, J. H.; Cross, A. D. J. Org. Chem. 1968, 33, 4176. (k) Windholz, T. B.; Brown, R. D. J. Org. Chem. 1972, 37, 1647. (l) Hurd, R. N.; Shah, D. H. J. Org. Chem. 1973, 38, 390. (m) Hurd, R. N.; Shah, D. H. J. Med. Chem. 1973, 16, 543. (n) Peters, C. A.; Hurd, R. N. J. Med. Chem. 1975, 18, 215. (o) Bass, R. J.; Banks, B. J.; Leeming, M. R. G.; Snarey, M. J. Chem. Soc. Perkin Trans. 1 1981, 124. (p) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem. 1998, 110, 2677.
74. For synthetic studies on the zearalenone family of macrolides see the following for leading references: (a) Keinan, E.; Sinha, S. C.; Sinha-Bagchi, A. J. Chem. Soc. Pertin 1 1991, 3333. (b) Hitchcock, S. A.; Pattenden, G. J. Chem. Soc. Perkin Trans. 1 1992, 1323. (c) Takahashi, T.; Nagashima, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1982, 23, 4361. (d) Takahashi, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1981, 22, 1363. (e) Kalivretenos, A.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883. (f) Rama Rao, A. V.; Deshmukh, M. N.; Sharma, G. V. M. Tetrahedron 1987, 43, 779. (g) Takahashi, T.; Kasuga, K.; Takahashi, M.; Tsuji, J. J. Am. Chem. Soc. 1979, 101, 5072. (h) Solladié, G.; Maestro, M. C.; Rubio, A.; Pedregal, C.; Carreno, M. C; Garcia Ruano, J. L. J. Org. Chem. 1991, 56, 2317. (i) Taub, D.; Girothra, N. N.; Hoffsommer, R. D.; Kuo, C. H.; Slates, H. L.; Weber, S.; Wendler, N. L. Tetrahedron 1968, 24, 2443. (j) Vlattas, I.; Harrison, I. T.; Tökes, L.; Fried, J. H.; Cross, A. D. J. Org. Chem. 1968, 33, 4176. (k) Windholz, T. B.; Brown, R. D. J. Org. Chem. 1972, 37, 1647. (l) Hurd, R. N.; Shah, D. H. J. Org. Chem. 1973, 38, 390. (m) Hurd, R. N.; Shah, D. H. J. Med. Chem. 1973, 16, 543. (n) Peters, C. A.; Hurd, R. N. J. Med. Chem. 1975, 18, 215. (o) Bass, R. J.; Banks, B. J.; Leeming, M. R. G.; Snarey, M. J. Chem. Soc. Perkin Trans. 1 1981, 124. (p) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem. 1998, 110, 2677.
75. For synthetic studies on the zearalenone family of macrolides see the following for leading references: (a) Keinan, E.; Sinha, S. C.; Sinha-Bagchi, A. J. Chem. Soc. Pertin 1 1991, 3333. (b) Hitchcock, S. A.; Pattenden, G. J. Chem. Soc. Perkin Trans. 1 1992, 1323. (c) Takahashi, T.; Nagashima, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1982, 23, 4361. (d) Takahashi, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1981, 22, 1363. (e) Kalivretenos, A.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883. (f) Rama Rao, A. V.; Deshmukh, M. N.; Sharma, G. V. M. Tetrahedron 1987, 43, 779. (g) Takahashi, T.; Kasuga, K.; Takahashi, M.; Tsuji, J. J. Am. Chem. Soc. 1979, 101, 5072. (h) Solladié, G.; Maestro, M. C.; Rubio, A.; Pedregal, C.; Carreno, M. C; Garcia Ruano, J. L. J. Org. Chem. 1991, 56, 2317. (i) Taub, D.; Girothra, N. N.; Hoffsommer, R. D.; Kuo, C. H.; Slates, H. L.; Weber, S.; Wendler, N. L. Tetrahedron 1968, 24, 2443. (j) Vlattas, I.; Harrison, I. T.; Tökes, L.; Fried, J. H.; Cross, A. D. J. Org. Chem. 1968, 33, 4176. (k) Windholz, T. B.; Brown, R. D. J. Org. Chem. 1972, 37, 1647. (l) Hurd, R. N.; Shah, D. H. J. Org. Chem. 1973, 38, 390. (m) Hurd, R. N.; Shah, D. H. J. Med. Chem. 1973, 16, 543. (n) Peters, C. A.; Hurd, R. N. J. Med. Chem. 1975, 18, 215. (o) Bass, R. J.; Banks, B. J.; Leeming, M. R. G.; Snarey, M. J. Chem. Soc. Perkin Trans. 1 1981, 124. (p) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem. 1998, 110, 2677.
76. For synthetic studies on the zearalenone family of macrolides see the following for leading references: (a) Keinan, E.; Sinha, S. C.; Sinha-Bagchi, A. J. Chem. Soc. Pertin 1 1991, 3333. (b) Hitchcock, S. A.; Pattenden, G. J. Chem. Soc. Perkin Trans. 1 1992, 1323. (c) Takahashi, T.; Nagashima, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1982, 23, 4361. (d) Takahashi, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1981, 22, 1363. (e) Kalivretenos, A.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883. (f) Rama Rao, A. V.; Deshmukh, M. N.; Sharma, G. V. M. Tetrahedron 1987, 43, 779. (g) Takahashi, T.; Kasuga, K.; Takahashi, M.; Tsuji, J. J. Am. Chem. Soc. 1979, 101, 5072. (h) Solladié, G.; Maestro, M. C.; Rubio, A.; Pedregal, C.; Carreno, M. C; Garcia Ruano, J. L. J. Org. Chem. 1991, 56, 2317. (i) Taub, D.; Girothra, N. N.; Hoffsommer, R. D.; Kuo, C. H.; Slates, H. L.; Weber, S.; Wendler, N. L. Tetrahedron 1968, 24, 2443. (j) Vlattas, I.; Harrison, I. T.; Tökes, L.; Fried, J. H.; Cross, A. D. J. Org. Chem. 1968, 33, 4176. (k) Windholz, T. B.; Brown, R. D. J. Org. Chem. 1972, 37, 1647. (l) Hurd, R. N.; Shah, D. H. J. Org. Chem. 1973, 38, 390. (m) Hurd, R. N.; Shah, D. H. J. Med. Chem. 1973, 16, 543. (n) Peters, C. A.; Hurd, R. N. J. Med. Chem. 1975, 18, 215. (o) Bass, R. J.; Banks, B. J.; Leeming, M. R. G.; Snarey, M. J. Chem. Soc. Perkin Trans. 1 1981, 124. (p) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem. 1998, 110, 2677.
77. For synthetic studies on the zearalenone family of macrolides see the following for leading references: (a) Keinan, E.; Sinha, S. C.; Sinha-Bagchi, A. J. Chem. Soc. Pertin 1 1991, 3333. (b) Hitchcock, S. A.; Pattenden, G. J. Chem. Soc. Perkin Trans. 1 1992, 1323. (c) Takahashi, T.; Nagashima, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1982, 23, 4361. (d) Takahashi, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1981, 22, 1363. (e) Kalivretenos, A.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883. (f) Rama Rao, A. V.; Deshmukh, M. N.; Sharma, G. V. M. Tetrahedron 1987, 43, 779. (g) Takahashi, T.; Kasuga, K.; Takahashi, M.; Tsuji, J. J. Am. Chem. Soc. 1979, 101, 5072. (h) Solladié, G.; Maestro, M. C.; Rubio, A.; Pedregal, C.; Carreno, M. C; Garcia Ruano, J. L. J. Org. Chem. 1991, 56, 2317. (i) Taub, D.; Girothra, N. N.; Hoffsommer, R. D.; Kuo, C. H.; Slates, H. L.; Weber, S.; Wendler, N. L. Tetrahedron 1968, 24, 2443. (j) Vlattas, I.; Harrison, I. T.; Tökes, L.; Fried, J. H.; Cross, A. D. J. Org. Chem. 1968, 33, 4176. (k) Windholz, T. B.; Brown, R. D. J. Org. Chem. 1972, 37, 1647. (l) Hurd, R. N.; Shah, D. H. J. Org. Chem. 1973, 38, 390. (m) Hurd, R. N.; Shah, D. H. J. Med. Chem. 1973, 16, 543. (n) Peters, C. A.; Hurd, R. N. J. Med. Chem. 1975, 18, 215. (o) Bass, R. J.; Banks, B. J.; Leeming, M. R. G.; Snarey, M. J. Chem. Soc. Perkin Trans. 1 1981, 124. (p) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem. 1998, 110, 2677.
78. For synthetic studies on the zearalenone family of macrolides see the following for leading references: (a) Keinan, E.; Sinha, S. C.; Sinha-Bagchi, A. J. Chem. Soc. Pertin 1 1991, 3333. (b) Hitchcock, S. A.; Pattenden, G. J. Chem. Soc. Perkin Trans. 1 1992, 1323. (c) Takahashi, T.; Nagashima, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1982, 23, 4361. (d) Takahashi, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1981, 22, 1363. (e) Kalivretenos, A.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883. (f) Rama Rao, A. V.; Deshmukh, M. N.; Sharma, G. V. M. Tetrahedron 1987, 43, 779. (g) Takahashi, T.; Kasuga, K.; Takahashi, M.; Tsuji, J. J. Am. Chem. Soc. 1979, 101, 5072. (h) Solladié, G.; Maestro, M. C.; Rubio, A.; Pedregal, C.; Carreno, M. C; Garcia Ruano, J. L. J. Org. Chem. 1991, 56, 2317. (i) Taub, D.; Girothra, N. N.; Hoffsommer, R. D.; Kuo, C. H.; Slates, H. L.; Weber, S.; Wendler, N. L. Tetrahedron 1968, 24, 2443. (j) Vlattas, I.; Harrison, I. T.; Tökes, L.; Fried, J. H.; Cross, A. D. J. Org. Chem. 1968, 33, 4176. (k) Windholz, T. B.; Brown, R. D. J. Org. Chem. 1972, 37, 1647. (l) Hurd, R. N.; Shah, D. H. J. Org. Chem. 1973, 38, 390. (m) Hurd, R. N.; Shah, D. H. J. Med. Chem. 1973, 16, 543. (n) Peters, C. A.; Hurd, R. N. J. Med. Chem. 1975, 18, 215. (o) Bass, R. J.; Banks, B. J.; Leeming, M. R. G.; Snarey, M. J. Chem. Soc. Perkin Trans. 1 1981, 124. (p) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem. 1998, 110, 2677.
79. For synthetic studies on the zearalenone family of macrolides see the following for leading references: (a) Keinan, E.; Sinha, S. C.; Sinha-Bagchi, A. J. Chem. Soc. Pertin 1 1991, 3333. (b) Hitchcock, S. A.; Pattenden, G. J. Chem. Soc. Perkin Trans. 1 1992, 1323. (c) Takahashi, T.; Nagashima, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1982, 23, 4361. (d) Takahashi, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1981, 22, 1363. (e) Kalivretenos, A.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883. (f) Rama Rao, A. V.; Deshmukh, M. N.; Sharma, G. V. M. Tetrahedron 1987, 43, 779. (g) Takahashi, T.; Kasuga, K.; Takahashi, M.; Tsuji, J. J. Am. Chem. Soc. 1979, 101, 5072. (h) Solladié, G.; Maestro, M. C.; Rubio, A.; Pedregal, C.; Carreno, M. C; Garcia Ruano, J. L. J. Org. Chem. 1991, 56, 2317. (i) Taub, D.; Girothra, N. N.; Hoffsommer, R. D.; Kuo, C. H.; Slates, H. L.; Weber, S.; Wendler, N. L. Tetrahedron 1968, 24, 2443. (j) Vlattas, I.; Harrison, I. T.; Tökes, L.; Fried, J. H.; Cross, A. D. J. Org. Chem. 1968, 33, 4176. (k) Windholz, T. B.; Brown, R. D. J. Org. Chem. 1972, 37, 1647. (l) Hurd, R. N.; Shah, D. H. J. Org. Chem. 1973, 38, 390. (m) Hurd, R. N.; Shah, D. H. J. Med. Chem. 1973, 16, 543. (n) Peters, C. A.; Hurd, R. N. J. Med. Chem. 1975, 18, 215. (o) Bass, R. J.; Banks, B. J.; Leeming, M. R. G.; Snarey, M. J. Chem. Soc. Perkin Trans. 1 1981, 124. (p) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem. 1998, 110, 2677.
80. For synthetic studies on the zearalenone family of macrolides see the following for leading references: (a) Keinan, E.; Sinha, S. C.; Sinha-Bagchi, A. J. Chem. Soc. Pertin 1 1991, 3333. (b) Hitchcock, S. A.; Pattenden, G. J. Chem. Soc. Perkin Trans. 1 1992, 1323. (c) Takahashi, T.; Nagashima, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1982, 23, 4361. (d) Takahashi, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1981, 22, 1363. (e) Kalivretenos, A.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883. (f) Rama Rao, A. V.; Deshmukh, M. N.; Sharma, G. V. M. Tetrahedron 1987, 43, 779. (g) Takahashi, T.; Kasuga, K.; Takahashi, M.; Tsuji, J. J. Am. Chem. Soc. 1979, 101, 5072. (h) Solladié, G.; Maestro, M. C.; Rubio, A.; Pedregal, C.; Carreno, M. C; Garcia Ruano, J. L. J. Org. Chem. 1991, 56, 2317. (i) Taub, D.; Girothra, N. N.; Hoffsommer, R. D.; Kuo, C. H.; Slates, H. L.; Weber, S.; Wendler, N. L. Tetrahedron 1968, 24, 2443. (j) Vlattas, I.; Harrison, I. T.; Tökes, L.; Fried, J. H.; Cross, A. D. J. Org. Chem. 1968, 33, 4176. (k) Windholz, T. B.; Brown, R. D. J. Org. Chem. 1972, 37, 1647. (l) Hurd, R. N.; Shah, D. H. J. Org. Chem. 1973, 38, 390. (m) Hurd, R. N.; Shah, D. H. J. Med. Chem. 1973, 16, 543. (n) Peters, C. A.; Hurd, R. N. J. Med. Chem. 1975, 18, 215. (o) Bass, R. J.; Banks, B. J.; Leeming, M. R. G.; Snarey, M. J. Chem. Soc. Perkin Trans. 1 1981, 124. (p) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem. 1998, 110, 2677.
81. For synthetic studies on the zearalenone family of macrolides see the following for leading references: (a) Keinan, E.; Sinha, S. C.; Sinha-Bagchi, A. J. Chem. Soc. Pertin 1 1991, 3333. (b) Hitchcock, S. A.; Pattenden, G. J. Chem. Soc. Perkin Trans. 1 1992, 1323. (c) Takahashi, T.; Nagashima, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1982, 23, 4361. (d) Takahashi, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1981, 22, 1363. (e) Kalivretenos, A.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883. (f) Rama Rao, A. V.; Deshmukh, M. N.; Sharma, G. V. M. Tetrahedron 1987, 43, 779. (g) Takahashi, T.; Kasuga, K.; Takahashi, M.; Tsuji, J. J. Am. Chem. Soc. 1979, 101, 5072. (h) Solladié, G.; Maestro, M. C.; Rubio, A.; Pedregal, C.; Carreno, M. C; Garcia Ruano, J. L. J. Org. Chem. 1991, 56, 2317. (i) Taub, D.; Girothra, N. N.; Hoffsommer, R. D.; Kuo, C. H.; Slates, H. L.; Weber, S.; Wendler, N. L. Tetrahedron 1968, 24, 2443. (j) Vlattas, I.; Harrison, I. T.; Tökes, L.; Fried, J. H.; Cross, A. D. J. Org. Chem. 1968, 33, 4176. (k) Windholz, T. B.; Brown, R. D. J. Org. Chem. 1972, 37, 1647. (l) Hurd, R. N.; Shah, D. H. J. Org. Chem. 1973, 38, 390. (m) Hurd, R. N.; Shah, D. H. J. Med. Chem. 1973, 16, 543. (n) Peters, C. A.; Hurd, R. N. J. Med. Chem. 1975, 18, 215. (o) Bass, R. J.; Banks, B. J.; Leeming, M. R. G.; Snarey, M. J. Chem. Soc. Perkin Trans. 1 1981, 124. (p) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem. 1998, 110, 2677.
82. For synthetic studies on the zearalenone family of macrolides see the following for leading references: (a) Keinan, E.; Sinha, S. C.; Sinha-Bagchi, A. J. Chem. Soc. Pertin 1 1991, 3333. (b) Hitchcock, S. A.; Pattenden, G. J. Chem. Soc. Perkin Trans. 1 1992, 1323. (c) Takahashi, T.; Nagashima, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1982, 23, 4361. (d) Takahashi, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1981, 22, 1363. (e) Kalivretenos, A.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883. (f) Rama Rao, A. V.; Deshmukh, M. N.; Sharma, G. V. M. Tetrahedron 1987, 43, 779. (g) Takahashi, T.; Kasuga, K.; Takahashi, M.; Tsuji, J. J. Am. Chem. Soc. 1979, 101, 5072. (h) Solladié, G.; Maestro, M. C.; Rubio, A.; Pedregal, C.; Carreno, M. C; Garcia Ruano, J. L. J. Org. Chem. 1991, 56, 2317. (i) Taub, D.; Girothra, N. N.; Hoffsommer, R. D.; Kuo, C. H.; Slates, H. L.; Weber, S.; Wendler, N. L. Tetrahedron 1968, 24, 2443. (j) Vlattas, I.; Harrison, I. T.; Tökes, L.; Fried, J. H.; Cross, A. D. J. Org. Chem. 1968, 33, 4176. (k) Windholz, T. B.; Brown, R. D. J. Org. Chem. 1972, 37, 1647. (l) Hurd, R. N.; Shah, D. H. J. Org. Chem. 1973, 38, 390. (m) Hurd, R. N.; Shah, D. H. J. Med. Chem. 1973, 16, 543. (n) Peters, C. A.; Hurd, R. N. J. Med. Chem. 1975, 18, 215. (o) Bass, R. J.; Banks, B. J.; Leeming, M. R. G.; Snarey, M. J. Chem. Soc. Perkin Trans. 1 1981, 124. (p) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem. 1998, 110, 2677.
83. For synthetic studies on the zearalenone family of macrolides see the following for leading references: (a) Keinan, E.; Sinha, S. C.; Sinha-Bagchi, A. J. Chem. Soc. Pertin 1 1991, 3333. (b) Hitchcock, S. A.; Pattenden, G. J. Chem. Soc. Perkin Trans. 1 1992, 1323. (c) Takahashi, T.; Nagashima, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1982, 23, 4361. (d) Takahashi, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1981, 22, 1363. (e) Kalivretenos, A.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883. (f) Rama Rao, A. V.; Deshmukh, M. N.; Sharma, G. V. M. Tetrahedron 1987, 43, 779. (g) Takahashi, T.; Kasuga, K.; Takahashi, M.; Tsuji, J. J. Am. Chem. Soc. 1979, 101, 5072. (h) Solladié, G.; Maestro, M. C.; Rubio, A.; Pedregal, C.; Carreno, M. C; Garcia Ruano, J. L. J. Org. Chem. 1991, 56, 2317. (i) Taub, D.; Girothra, N. N.; Hoffsommer, R. D.; Kuo, C. H.; Slates, H. L.; Weber, S.; Wendler, N. L. Tetrahedron 1968, 24, 2443. (j) Vlattas, I.; Harrison, I. T.; Tökes, L.; Fried, J. H.; Cross, A. D. J. Org. Chem. 1968, 33, 4176. (k) Windholz, T. B.; Brown, R. D. J. Org. Chem. 1972, 37, 1647. (l) Hurd, R. N.; Shah, D. H. J. Org. Chem. 1973, 38, 390. (m) Hurd, R. N.; Shah, D. H. J. Med. Chem. 1973, 16, 543. (n) Peters, C. A.; Hurd, R. N. J. Med. Chem. 1975, 18, 215. (o) Bass, R. J.; Banks, B. J.; Leeming, M. R. G.; Snarey, M. J. Chem. Soc. Perkin Trans. 1 1981, 124. (p) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem. 1998, 110, 2677.
84. For synthetic studies on the zearalenone family of macrolides see the following for leading references: (a) Keinan, E.; Sinha, S. C.; Sinha-Bagchi, A. J. Chem. Soc. Pertin 1 1991, 3333. (b) Hitchcock, S. A.; Pattenden, G. J. Chem. Soc. Perkin Trans. 1 1992, 1323. (c) Takahashi, T.; Nagashima, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1982, 23, 4361. (d) Takahashi, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1981, 22, 1363. (e) Kalivretenos, A.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883. (f) Rama Rao, A. V.; Deshmukh, M. N.; Sharma, G. V. M. Tetrahedron 1987, 43, 779. (g) Takahashi, T.; Kasuga, K.; Takahashi, M.; Tsuji, J. J. Am. Chem. Soc. 1979, 101, 5072. (h) Solladié, G.; Maestro, M. C.; Rubio, A.; Pedregal, C.; Carreno, M. C; Garcia Ruano, J. L. J. Org. Chem. 1991, 56, 2317. (i) Taub, D.; Girothra, N. N.; Hoffsommer, R. D.; Kuo, C. H.; Slates, H. L.; Weber, S.; Wendler, N. L. Tetrahedron 1968, 24, 2443. (j) Vlattas, I.; Harrison, I. T.; Tökes, L.; Fried, J. H.; Cross, A. D. J. Org. Chem. 1968, 33, 4176. (k) Windholz, T. B.; Brown, R. D. J. Org. Chem. 1972, 37, 1647. (l) Hurd, R. N.; Shah, D. H. J. Org. Chem. 1973, 38, 390. (m) Hurd, R. N.; Shah, D. H. J. Med. Chem. 1973, 16, 543. (n) Peters, C. A.; Hurd, R. N. J. Med. Chem. 1975, 18, 215. (o) Bass, R. J.; Banks, B. J.; Leeming, M. R. G.; Snarey, M. J. Chem. Soc. Perkin Trans. 1 1981, 124. (p) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem. 1998, 110, 2677.
85. For synthetic studies on the zearalenone family of macrolides see the following for leading references: (a) Keinan, E.; Sinha, S. C.; Sinha-Bagchi, A. J. Chem. Soc. Pertin 1 1991, 3333. (b) Hitchcock, S. A.; Pattenden, G. J. Chem. Soc. Perkin Trans. 1 1992, 1323. (c) Takahashi, T.; Nagashima, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1982, 23, 4361. (d) Takahashi, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1981, 22, 1363. (e) Kalivretenos, A.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883. (f) Rama Rao, A. V.; Deshmukh, M. N.; Sharma, G. V. M. Tetrahedron 1987, 43, 779. (g) Takahashi, T.; Kasuga, K.; Takahashi, M.; Tsuji, J. J. Am. Chem. Soc. 1979, 101, 5072. (h) Solladié, G.; Maestro, M. C.; Rubio, A.; Pedregal, C.; Carreno, M. C; Garcia Ruano, J. L. J. Org. Chem. 1991, 56, 2317. (i) Taub, D.; Girothra, N. N.; Hoffsommer, R. D.; Kuo, C. H.; Slates, H. L.; Weber, S.; Wendler, N. L. Tetrahedron 1968, 24, 2443. (j) Vlattas, I.; Harrison, I. T.; Tökes, L.; Fried, J. H.; Cross, A. D. J. Org. Chem. 1968, 33, 4176. (k) Windholz, T. B.; Brown, R. D. J. Org. Chem. 1972, 37, 1647. (l) Hurd, R. N.; Shah, D. H. J. Org. Chem. 1973, 38, 390. (m) Hurd, R. N.; Shah, D. H. J. Med. Chem. 1973, 16, 543. (n) Peters, C. A.; Hurd, R. N. J. Med. Chem. 1975, 18, 215. (o) Bass, R. J.; Banks, B. J.; Leeming, M. R. G.; Snarey, M. J. Chem. Soc. Perkin Trans. 1 1981, 124. (p) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem. 1998, 110, 2677.
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